Hypervalent iodine chemistry in organic synthesis
This Thematic Series on Hypervalent Iodine Chemistry covers all aspects and highlights current developments of this area. New insights have led to many research activities during the last years, which are clearly reflected in the many high quality contributions assembled in this series. Theoretical work is underpinning the development of novel compounds and catalysts, which have now already been established as powerful metal-free reagents. Their applications in many different areas of chemistry have shown that they often outperform traditional procedures and even allowing new and unusual reactions to take place.
- Full Research Paper
- Published 05 Feb 2018
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Scheme 1: One-pot preparation of 4-aryl-3-bromocoumarins 3 from 3-aryl-2-propynoic acids 1 with diphenyliodon...
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Scheme 2: One-pot preparation of 3-bromo-4-phenylcoumarins 3a from 3-phenyl-2-propynoic acid (1a) with daryli...
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Scheme 3: Derivatization of 3-bromo-4-phenylcoumarin.
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Figure 1: ORTEP of 3-bromo-7-chloro-4-phenylcoumarin (3Da).
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Scheme 4: Possible reaction pathway.
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- Letter
- Published 06 Feb 2018
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Scheme 1: Arylations of pyrrole derivatives with diaryliodonium salts.
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Scheme 2: Formation of N-phenylamine derivatives 4 and 5 via ring opening reactions.
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Scheme 3: Preparation of product 6 by hydrogenation.
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- Published 07 Feb 2018
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Figure 1: Compounds used for the biological study.
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Figure 2: Compounds 1–4 induced cell death in U937 cells. Briefly, U937 cells (1 × 104 cells/mL) were incubat...
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Scheme 1: Synthesis of pentafluoro-(2-iodophenyl)-λ6-sulfane (7).
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Scheme 2: Synthesis of unsymmetrical ortho-SF5 diaryliodonium salts 3p, 4b, 5a and 6a.
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Figure 3: X-ray crystallographic structure of 3p drawn at 50% probability (CCDC 1573953).
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Figure 4: Ortho-SF5 phenyl iodonium salts 3p and 5a and their structural components 7 and 9 induced cell deat...
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Figure 5: 3k, 3m and 3p induced cell death in AGLCL, a human normal B cell line. Briefly, AGLCL cells (1 × 104...
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- Letter
- Published 28 Feb 2018
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Scheme 1: Hetero-Diels–Alder (HDA) reactions of N-acylnitroso species.
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Scheme 2: DIB-mediated oxidative HDA reactions of 1a–c with various guaiacols.
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- Letter
- Published 20 Mar 2018
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Scheme 1: Enantioselective dioxytosylation of styrene as a seminal example.
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Figure 1: Series of lactate-based hypervalent iodine reagents.
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Scheme 2: Plausible pathways in dioxytosylation of styrenes.
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- Letter
- Published 09 Apr 2018
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Scheme 1: Reactions of substituted allenes with HVI reagents.
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Scheme 2: Chlorination of p-tolylallene (2a) with (dichloroiodo)benzene (1a).
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Scheme 3: Chlorination of various aryl-substituted allenes. General conditions: Allene 2a (0.2 mmol, 1 equiv)...
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Scheme 4: Chlorination of various α-substituted phenylallene derivatives. General conditions: Allene 2a (0.2 ...
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Scheme 5: Chlorination of methoxy-substituted α-methyl phenylallenes. General conditions: Allene 2a (0.2 mmol...
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Scheme 6: Control reactions: (a) chlorination of deuterated biphenylallene [D2]-2b; (b) reaction with TEMPO.
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Figure 1: Proposed reaction mechanism.
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- Full Research Paper
- Published 12 Apr 2018
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- Full Research Paper
- Published 30 Apr 2018
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Figure 1: Structures of pentavalent iodine oxidants 1 and 2, and iodine catalysts 3–13.
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Figure 2: Structures of the catalysts 16–25.
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Scheme 1: Oxidation of the monovalent iodine derivatives 17 and 3 to the pentavalent iodine derivatives 29 an...
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Figure 3: Reaction profile of the oxidation of (a) iodobenzamide 17 and (b) 2-iodobenzoic acid (3) with Oxone®...
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Scheme 2: Plausible reaction mechanism for the oxidation of alcohols catalyzed by the 2-iodobenzamides.
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- Published 03 May 2018
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Scheme 1: Oxidative intermolecular cross-coupling of dissimilar enolates.
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Scheme 2: Scope of the homo- and heterocoupling of enolates. The purple bond indicates the bond formed. The b...
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Scheme 3: Study of diastereoselectivity of the cross-coupling reaction.
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- Published 08 May 2018
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Scheme 1: Representative examples of benziodoxoles and benziodazoles.
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Scheme 2: Preparation of bicyclic benziodazole 7a.
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Figure 1: X-ray crystal structure of compound 7a. Ellipsoids are drawn to the 50% probability level. Selected...
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Scheme 3: Benziodadiazole 7a mediated oxidatively assisted esterification and amidation reactions.
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- Published 09 May 2018
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Figure 1: Selected examples of bioactive compounds containing the 2-oxazoline motif.
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Figure 2: The catalytic difluorination of alkenes (top) and the proposed fluorocyclisation via the same I(I)/...
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Figure 3: Substrate scope. aReaction conducted on 1 mmol scale. bReaction time increased to 40 hours. cReacti...
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Scheme 1: Exploring diastereocontrol and the synthesis of the fluorohydrin 3. Yields in parentheses were dete...
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Figure 4: X-ray molecular structure of compound 2c. Thermal ellipsoids shown at the 50% propability level. To...
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- Letter
- Published 11 May 2018
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Scheme 1: Hypervalent iodine-mediated heterofunctionalization of terminal alkenes.
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Scheme 2: Substrate scope of the Ritter-type oxyamidation: isoxazoline synthesis. All reactions were performe...
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Scheme 3: Substrate scope of Ritter-type amido-amidation: pyrazoline synthesis. All reactions were performed ...
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Scheme 4: Plausible mechanism of the hypervalent iodine(III)-mediated Ritter-type oxyamidation/amido-amidatio...
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- Letter
- Published 11 May 2018
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Scheme 1: Imides as an important scaffold.
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Scheme 2: Scope of compatible aryl groups. Conditions: 1 (0.5 mmol, 1 equiv), potassium phthalimide (2.5 mmol...
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Scheme 3: One-pot synthesis of anilines.
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- Full Research Paper
- Published 14 May 2018
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Scheme 1: Examples of the reductive iodonio-Claisen rearrangement compared to new reactivity seen with benzyl...
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Scheme 2: Crossover reaction experiments.
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Scheme 3: Suggested mechanism based on product formation and crossover experiments.
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Scheme 4: Proposed mechanism for the generation of 2i from Table 2, entry 8.
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- Published 15 May 2018
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Scheme 1: Decarboxylative functionalization using PhI(OAc)2/I2 system.
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Scheme 2: Substrate scope. Reactions were conducted on a 0.5 mmol scale at a 0.2 or 0.4 M concentration on th...
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Scheme 3: Hydrolysis of acetates.
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Scheme 4: Mechanistic investigations.
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Scheme 5: Proposed reaction pathway.
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- Letter
- Published 16 May 2018
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Scheme 1: Hypervalent iodine(III)-induced benzylic C–H functionalization for oxidative coupling with carboxyl...
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Scheme 2: Radical reactivities of the I(III)–Br bond generated from PIDA.
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Scheme 3: Benzylic C–H carboxylations by the iodosobenzene/NaBr system.
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Scheme 4: Outline of the proposed reaction mechanism for the PIDA/NaBr system.
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Scheme 5: Reaction of benzyl bromide 2h’ under radical C–H acetoxylation conditions.
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- Published 18 May 2018
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Figure 1: Halogenated terpenoids from natural sources.
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Scheme 1: Previously developed bromo-functionalizations of polyprenoids using iodine(III) reagents.
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Figure 2: Selected monoterpenoids used in this study.
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Scheme 2: Dibromination of acyclic monoterpenoids.
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Scheme 3: Bromo(trifluoro)acetoxylation of acyclic monoterpenoids.
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Scheme 4: Bromohydroxylation of acyclic monoterpenoids.
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Scheme 5: Iodo(trifluoro)acetoxylation of acyclic monoterpenoids.
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Scheme 6: Chlorination of acyclic monoterpenoids.
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Scheme 7: General mechanism proposal for the formation of 2–6 and control experiments.
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- Published 22 May 2018
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Figure 1: Iodosodilactone and FPID.
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Scheme 1: Proposed mechanism for FPID-mediated amide bond formation.
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Scheme 2: Solid-phase peptide synthesis mediated by FPID/(4-MeOC6H4)3P. Conditions: The resin loading for 2-C...
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Scheme 3: The regeneration of FPID after SPPS.
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Figure 2: Structure of pseudostellarin D.
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Scheme 4: Synthetic strategies of pseudostellarin D.
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Scheme 5: Preparation of the precursor of pseudostellarin D.
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- Letter
- Published 24 May 2018
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Scheme 1: Mechanistic hypothesis.
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Scheme 2: Extension of the method.
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Scheme 3: Carbon-based nucleophiles.
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Scheme 4: THF ring opening.
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- Letter
- Published 25 May 2018
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Figure 1: Bioactive compounds with pyridinone, quinolone and indole cores.
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Scheme 1: C–H functionalization of pyridinones and quinoline N-oxides.
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Scheme 2: Scope and limitations of the Rh-catalyzed C–H activation of [1,2'-bipyridin]-2-one.
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Scheme 3: Scope of the Rh-catalyzed peri C–H activation of quinoline N-oxides.
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Scheme 4: Product modifications.
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- Published 28 May 2018
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Scheme 1: Investigation of alkynylbenziodoxole derivatives for radical alkynylations.
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Scheme 2: Synthesis and characterization of BI-alkyne derivatives 3a–f.
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Scheme 3: Reaction of alkynylbenziodoxole derivatives for deboronative alkynylation in photoredox catalysis. ...
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Scheme 4: Reaction of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis. Reac...
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Scheme 5: Reaction of alkynylbenziodoxole derivatives for acyl radical alkynylation in photoredox catalysis. ...
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Scheme 6: Mechanistic investigations of alkynylbenziodoxole for radical acceptor and oxidative quenching reac...
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Scheme 7: The role of alkynylbenziodoxole derivatives for radical alkynylation in photoredox catalysis.
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- Review
- Published 30 May 2018
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Scheme 1: An overview of different chiral iodine reagents or precursors thereof.
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Scheme 2: Asymmetric oxidation of sulfides by chiral hypervalent iodine reagents.
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Scheme 3: Oxidative dearomatization of naphthol derivatives by Kita et al.
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Scheme 4: [4 + 2] Diels–Alder dimerization reported by Birman et al.
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Scheme 5: m-CPBA guided catalytic oxidative naphthol dearomatization.
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Scheme 6: Oxidative dearomatization of phenolic derivatives by Ishihara et al.
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Scheme 7: Oxidative spirocyclization applying precatalyst 11 developed by Ciufolini et al.
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Scheme 8: Asymmetric hydroxylative dearomatization.
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Scheme 9: Enantioselective oxylactonization reported by Fujita et al.
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Scheme 10: Dioxytosylation of styrene (47) by Wirth et al.
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Scheme 11: Oxyarylation and aminoarylation of alkenes.
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Scheme 12: Asymmetric diamination of alkenes.
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Scheme 13: Stereoselective oxyamination of alkenes reported by Wirth et al.
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Scheme 14: Enantioselective and regioselective aminofluorination by Nevado et al.
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Scheme 15: Fluorinated difunctionalization reported by Jacobsen et al.
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Scheme 16: Aryl rearrangement reported by Wirth et al.
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Scheme 17: α-Arylation of β-ketoesters.
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Scheme 18: Asymmetric α-oxytosylation of carbonyls.
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Scheme 19: Asymmetric α-oxygenation and α-amination of carbonyls reported by Wirth et al.
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Scheme 20: Asymmetric α-functionalization of ketophenols using chiral quaternary ammonium (hypo)iodite salt re...
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Scheme 21: Oxidative Intramolecular coupling by Gong et al.
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Scheme 22: α-Sulfonyl and α-phosphoryl oxylation of ketones reported by Masson et al.
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Scheme 23: α-Fluorination of β-keto esters.
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Scheme 24: Alkynylation of β-ketoesters and amides catalyzed by phase-transfer catalyst.
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Scheme 25: Alkynylation of β-ketoesters and dearomative alkynylation of phenols.
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- Review
- Published 30 May 2018
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Scheme 1: Overview of different types of iodane-based group-transfer reactions and their atom economy based o...
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Scheme 2: (a) Structure of diaryliodonium salts 1. (b) Diarylation of a suitable substrate A with one equival...
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Scheme 3: Synthesis of biphenyls 3 and 3’ with symmetrical diaryliodonium salts 1.
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Scheme 4: Synthesis of diaryl thioethers 5.
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Scheme 5: Synthesis of two distinct S-aryl dithiocarbamates 7 and 7’ from one equivalent of diaryliodonium sa...
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Scheme 6: Synthesis of substituted isoindolin-1-ones 9 from 2-formylbenzonitrile 8 and the postulated reactio...
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Scheme 7: Domino C-/N-arylation of indoles 10.
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Scheme 8: Domino modification of N-heterocycles 12 via in situ-generated directing groups.
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Scheme 9: Synthesis of triarylamines 17 through a double arylation of anilines.
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Scheme 10: Selective conversion of novel aryl(imidazolyl)iodonium salts 1b to 1,5-disubstituted imidazoles 18.
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Scheme 11: Selected examples for the application of cyclic diaryliodonium salts 19.
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Scheme 12: Tandem oxidation–arylation sequence with (dicarboxyiodo)benzenes 20.
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Scheme 13: Oxidative α-arylation via the transfer of an intact 2-iodoaryl group.
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Scheme 14: Tandem ortho-iodination/O-arylation cascade with PIDA derivatives 20b.
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Scheme 15: Synthesis of meta-N,N-diarylaminophenols 28 and the postulated mechanism.
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Scheme 16: (Dicarboxyiodo)benzene-mediated metal-catalysed C–H amination and arylation.
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Scheme 17: Postulated mechanism for the amination–arylation sequence.
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Scheme 18: Auto-amination and cross-coupling of PIDA derivatives 20c.
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Scheme 19: Tandem C(sp3)–H olefination/C(sp2)–H arylation.
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Scheme 20: Atom efficient functionalisations with benziodoxolones 36.
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Scheme 21: Atom-efficient synthesis of furans 39 from benziodoxolones 36a and their further derivatisations.
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Scheme 22: Oxyalkynylation of diazo compounds 42.
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Scheme 23: Enantioselective oxyalkynylation of diazo compounds 42’.
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Scheme 24: Iron-catalysed oxyazidation of enamides 45.
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- Full Research Paper
- Published 15 Jun 2018
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Figure 1: Representative pharmaceutical agents bearing the CF3 group.
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Figure 2: The structures of the Togni reagents 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (1) and trifluor...
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Scheme 1: Our previous hypervalent iodine-mediated synthesis of 2H-azirine compounds.
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Scheme 2: Study on the presumed Togni reagent 1-mediated trifluoromethylation followed by PhIO-mediated aziri...
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Scheme 3: Togni reagent/PhIO-mediated one-pot synthesis of β-trifluoromethyl 2H-azirines. Reaction conditions...
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Scheme 4: Control study with TEMPO.
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Scheme 5: Proposed mechanism for the Togni reagent-mediated trifluoromethylation of enamines.
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- Letter
- Published 20 Jun 2018
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Figure 1: Compounds containing a phenoxazine moiety.
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Scheme 1: Reported syntheses of phenoxazine derivatives.
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Scheme 2: Retrosynthesis of phenoxazine.
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Scheme 3: Synthesis of iodonium salt 5a.
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Scheme 4: Synthesis of iodonium salt 7.
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Scheme 5: O-Arylation via route B.
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Scheme 6: a) Cyclization of diaryl ether 3. b) Attempted one pot-synthesis of 2. aBased on recovered 3.
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Scheme 7: Formal synthesis of phenoxazine (1). aBased on recovered 3.
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- Review
- Published 21 Jun 2018
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Scheme 1: Strategies to address the issue of sustainability with polyvalent organoiodine reagents.
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Scheme 2: Functionalization of ketones and alkenes with IBX.
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Scheme 3: Functionalization of pyrroles with DMP.
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Scheme 4: Catalytic benzoyloxy-trifluoromethylation reported by Szabó.
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Scheme 5: Catalytic benzoyloxy-trifluoromethylation reported by Mideoka.
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Scheme 6: Catalytic 1,4-benzoyloxy-trifluoromethylation of dienes.
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Scheme 7: Catalytic benzoyloxy-trifluoromethylation of allylamines.
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Scheme 8: Catalytic benzoyloxy-trifluoromethylation of enynes.
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Scheme 9: Catalytic benzoyloxy-trifluoromethylation of allenes.
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Scheme 10: Alkynylation of N-(aryl)imines with EBX for the formation of furans.
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Scheme 11: Catalytic benzoyloxy-alkynylation of diazo compounds.
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Scheme 12: Catalytic asymmetric benzoyloxy-alkynylation of diazo compounds.
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Scheme 13: Catalytic 1,2-benzoyloxy-azidation of alkenes.
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Scheme 14: Catalytic 1,2-benzoyloxy-azidation of enamides.
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Scheme 15: Catalytic 1,2-benzoyloxy-iodination of alkenes.
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Scheme 16: Seminal study with cyclic diaryl-λ3-iodane.
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Scheme 17: Synthesis of alkylidenefluorenes from cyclic diaryl-λ3-iodanes.
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Scheme 18: Synthesis of alkyne-substituted alkylidenefluorenes.
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Scheme 19: Synthesis of phenanthrenes from cyclic diaryl-λ3-iodanes.
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Scheme 20: Synthesis of dibenzocarbazoles from cyclic diaryl-λ3-iodanes.
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Scheme 21: Synthesis of triazolophenantridines from cyclic diaryl-λ3-iodanes.
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Scheme 22: Synthesis of functionalized benzoxazoles from cyclic diaryl-λ3-iodanes.
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Scheme 23: Sequential difunctionalization of cyclic diaryl-λ3-iodanes.
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Scheme 24: Double Suzuki–Miyaura coupling reaction of cyclic diaryl-λ3-iodanes.
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Scheme 25: Synthesis of a δ-carboline from cyclic diaryl-λ3-iodane.
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Scheme 26: Synthesis of N-(aryl)carbazoles from cyclic diaryl-λ3-iodanes.
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Scheme 27: Synthesis of carbazoles from cyclic diaryl-λ3-iodanes.
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Scheme 28: Synthesis of carbazoles and acridines from cyclic diaryl-λ3-iodanes.
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Scheme 29: Synthesis of dibenzothiophenes from cyclic diaryl-λ3-iodanes.
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Scheme 30: Synthesis of various sulfur heterocycles from cyclic diaryl-λ3-iodanes.
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Scheme 31: Synthesis of dibenzothioheterocycles from cyclic diaryl-λ3-iodanes.
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Scheme 32: Synthesis of dibenzosulfides and dibenzoselenides from cyclic diaryl-λ3-iodanes.
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Scheme 33: Synthesis of dibenzosulfones from cyclic diaryl-λ3-iodanes.
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Scheme 34: Seminal study with linear diaryl-λ3-iodanes.
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Scheme 35: N-Arylation of benzotriazole with symmetrical diaryl-λ3-iodanes.
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Scheme 36: Tandem catalytic C–H/N–H arylation of indoles with diaryl-λ3-iodanes.
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Scheme 37: Tandem N-arylation/C(sp2)–H arylation with diaryl-λ3-iodanes.
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Scheme 38: Catalytic intermolecular diarylation of anilines with diaryl-λ3-iodanes.
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Scheme 39: Catalytic synthesis of diarylsulfides with diaryl-λ3-iodanes.
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Scheme 40: α-Arylation of enolates using [bis(trifluoroacetoxy)iodo]arenes.
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Scheme 41: Mechanism of the α-arylation using [bis(trifluoroacetoxy)iodo]arene.
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Scheme 42: Catalytic nitrene additions mediated by [bis(acyloxy)iodo]arenes.
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Scheme 43: Tandem of C(sp3)–H amination/sila-Sonogashira–Hagihara coupling.
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Scheme 44: Tandem reaction using a λ3-iodane as an oxidant, a substrate and a coupling partner.
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Scheme 45: Synthesis of 1,2-diarylated acrylamidines with ArI(OAc)2.
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- Review
- Published 28 Jun 2018
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Figure 1: Design of potential antineoplastic nucleosides.
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Scheme 1: Synthesis of 4’-thioDMDC.
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Scheme 2: Synthesis of 4’-thioribonucleosides by Minakawa and Matsuda.
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Scheme 3: Synthesis of 4’-thioribonucleosides by Yoshimura.
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Figure 2: Concept of the Pummerer-type glycosylation and hypervalent iodine-mediated glycosylation.
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Scheme 4: Oxidative glycosylation of 4-thioribose mediated by hypervalent iodine.
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Figure 3: Speculated mechanism of oxidative glycosylation mediated by hypervalent iodine.
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Scheme 5: Synthesis of purine 4’-thioribonucleosides using hypervalent iodine-mediated glycosylation.
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Scheme 6: Unexpected glycosylation of a thietanose derivative.
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Scheme 7: Speculated mechanism of the ring expansion of a thietanose derivative.
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Scheme 8: Synthesis of thietanonucleosides using the Pummerer-type glycosylation.
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Scheme 9: First synthesis of 4’-selenonucleosides.
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Scheme 10: The Pummerer-type glycosylation of 4-selenoxide 74.
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Scheme 11: Synthesis of purine 4’-selenonucleosides using hypervalent iodine-mediated glycosylation.
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Figure 4: Concept of the oxidative coupling reaction applicable to the synthesis of carbocyclic nucleosides.
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Scheme 12: Oxidative coupling reaction mediated by hypervalent iodine.
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Scheme 13: Synthesis of cyclohexenyl nucleosides using an oxidative coupling reaction.
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Figure 5: Concept of the oxidative coupling reaction of glycal derivatives.
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Scheme 14: Oxidative coupling reaction of silylated uracil and DHP using hypervalent iodine.
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Scheme 15: Proposed mechanism of the oxidative coupling reaction mediated by hypervalent iodine.
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Figure 6: Synthesis of 2’,3’-unsaturated nucleosides using hypervalent iodine and a co-catalyst.
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Scheme 16: Synthesis of dihydropyranonucleoside.
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Scheme 17: Synthesis of acetoxyacetals using hypervalent iodine and addition of silylated base.
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Scheme 18: One-pot fragmentation-nucleophilic additions mediated by hypervalent iodine.
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Figure 7: The reaction of thioglycoside with hypervalent iodine in the presence of Lewis acids.
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Scheme 19: Synthesis of disaccharides employing thioglycosides under an oxidative coupling reaction mediated b...
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Scheme 20: Synthesis of disaccharides using disarmed thioglycosides by hypervalent iodine-mediated glycosylati...
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Scheme 21: Glycosylation using aryl(trifluoroethyl)iodium triflimide.
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Figure 8: Expected mechanism of hypervalent iodine-mediated glycosylation with glycals.
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Scheme 22: Synthesis of oligosaccharides by hypervalent iodine-mediated glycosylation with glycals.
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Scheme 23: Synthesis of 2-deoxy amino acid glycosides.
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Figure 9: Rationale for the intramolecular migration of the amino acid unit.
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- Published 12 Jul 2018
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Scheme 1: Possible intermediates of the interaction of alkynyl compounds with Ar–Cu(III) species.
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Scheme 2: Two possible reaction routes for the oxazoline formation explored by computations. The schemes indi...
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Scheme 3: Free energy profiles for the possible reaction routes. The final energy state (−50.5 kcal/mol) is n...
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- Published 17 Jul 2018
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Figure 1: The structures of biologically active natural and synthetic products having spirocyclic moiety.
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Scheme 1: Iodine(III)-mediated spirocyclization of substituted phenols 7 and 11 to 10 and 13, respectively.
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Scheme 2: PIDA-mediated spirolactonization of N-protected tyrosine 14 to spirolactone 16.
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Figure 2: The structures of polymer-supported iodine(III) reagents 17a and 17b.
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Scheme 3: Spirolactonization of substrates 14 to spirolactones 16 using polymer-supported reagents 17a and 17b...
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Scheme 4: PIDA-mediated spirolactonization of 1-(p-hydroxyaryl)cyclobutanols 18 to spirolactones 19.
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Scheme 5: Iodine(III)-mediated spirocyclization of aryl alkynes 24 to spirolactones 26 by the reaction with b...
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Scheme 6: Bridged iodine(III)-mediated spirocyclization of phenols 27 to spirodienones 29.
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Scheme 7: Iodine(III)-mediated spirocyclization of arnottin I (30) to its spirocyclic analogue arnottin II (32...
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Scheme 8: Iodine(III)-catalyzed spirolactonization of p-substituted phenols 27 to spirolactones 29 using iodo...
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Scheme 9: Iodine(III)-catalyzed oxylactonization of ketocarboxylic acid 34 to spirolactone 36 using iodobenze...
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Scheme 10: Iodine(III)-mediated asymmetric oxidative spirocyclization of naphthyl acids 37 to naphthyl spirola...
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Scheme 11: Oxidative cyclization of L-tyrosine 14 to spirocyclic lactone 16 using PIDA (15).
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Scheme 12: Oxidative cyclization of oxazoline derivatives 41 to spirolactams 42 using PIDA (15).
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Scheme 13: Oxidative cyclization of oxazoline 43 to spirolactam 44 using PIDA 15 as oxidant.
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Scheme 14: PIFA-mediated spirocyclization of amides 46 to N-spirolactams 47 using PIFA (31) as an electrophile....
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Scheme 15: Synthesis of spirolactam 49 from phenolic enamide 48 using PIDA (15).
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Scheme 16: Iodine(III)-mediated spirocyclization of alkyl hydroxamates 50 to spirolactams 51 using stoichiomet...
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Scheme 17: PIFA-mediated cyclization of substrate 52 to spirocyclic product 54.
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Scheme 18: Synthesis of spiro β-lactams 56 by oxidative coupling reaction of p-substituted phenols 55 using PI...
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Scheme 19: Iodine(III)-mediated spirocyclization of para-substituted amide 58 to spirolactam 59 by the reactio...
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Scheme 20: Iodine(III)-mediated synthesis of spirolactams 61 from anilide derivatives 60.
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Scheme 21: PIFA-mediated oxidative cyclization of anilide 60 to bis-spirobisoxindole 61.
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Scheme 22: PIDA-mediated spirocyclization of phenylacetamides 65 to spirocyclic lactams 66.
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Scheme 23: Oxidative dearomatization of arylamines 67 with PIFA (31) to give dieniminium salts 68.
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Scheme 24: PIFA-mediated oxidative spirocarbocyclization of 4-methoxybenzamide 69 with diphenylacetylene (70) ...
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Scheme 25: Synthesis of spiroxyindole 75 using I2O5/TBHP oxidative system.
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Scheme 26: Iodine(III)-catalyzed spirolactonization of functionalized amides 76 to spirolactones 77 using iodo...
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Scheme 27: Intramolecular cyclization of alkenes 78 to spirolactams 80 using Pd(II) 79 and PIDA (15) as the ox...
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Scheme 28: Iodine(III)-catalyzed spiroaminocyclization of amides 76 to spirolactam 77 using bis(iodoarene) 81 ...
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Scheme 29: Iodine(III)-catalyzed spirolactonization of N-phenyl benzamides 82 to spirolactams 83 using iodoben...
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Scheme 30: Iodine(III)-mediated asymmetric oxidative spirocyclization of phenols 84 to spirolactams 86 using c...
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Scheme 31: Iodine(III)-catalyzed asymmetric oxidative spirocyclization of N-aryl naphthamides 87 to spirocycli...
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Scheme 32: Cyclization of p-substituted phenolic compound 89 to spirolactam 90 using PIDA (15) in TFE.
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Scheme 33: Iodine(III)-mediated synthesis of spirocyclic compound 93 from substrates 92 using PIDA (15) as an ...
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Scheme 34: Iodine(III)-mediated spirocyclization of p-substituted phenol 48 to spirocyclic compound 49 using P...
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Scheme 35: Bridged iodine(III)-mediated spirocyclization of O-silylated phenolic compound 96 in the synthesis ...
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Scheme 36: PIFA-mediated approach for the spirocyclization of ortho-substituted phenols 98 to aza-spirocarbocy...
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Scheme 37: Oxidative cyclization of para-substituted phenols 102 to spirocarbocyclic compounds 104 using Koser...
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Scheme 38: Iodine(III)-mediated spirocyclization of aryl alkynes 105 to spirocarbocyclic compound 106 by the r...
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Scheme 39: Iodine(III)-mediated spirocarbocyclization of ortho-substituted phenols 107 to spirocarbocyclic com...
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Scheme 40: PIFA-mediated oxidative cyclization of substrates 110 to spirocarbocyclic compounds 111.
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Scheme 41: Iodine(III)-mediated cyclization of substrate 113 to spirocyclic compound 114.
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Scheme 42: Iodine(III)-mediated spirocyclization of phenolic substrate 116 to the spirocarbocyclic natural pro...
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Scheme 43: Iodine(III)-catalyzed spirocyclization of phenols 117 to spirocarbocyclic products 119 using iodoar...
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Scheme 44: PIFA-mediated spirocyclization of 110 to spirocyclic compound 111 using PIFA (31) as electrophile.
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Scheme 45: PIDA-mediated spirocyclization of phenolic sulfonamide 122 to spiroketones 123.
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Scheme 46: Iodine(III)-mediated oxidative spirocyclization of 2-naphthol derivatives 124 to spiropyrrolidines ...
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Scheme 47: PIDA-mediated oxidative spirocyclization of m-substituted phenols 126 to tricyclic spiroketals 127.
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Figure 3: The structures of chiral organoiodine(III) catalysts 129a and 129b.
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Scheme 48: Iodine(III)-catalyzed oxidative spirocyclization of substituted phenols 128 to spirocyclic ketals 1...
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Scheme 49: Oxidative spirocyclization of para-substituted phenol 131 to spirodienone 133 using polymer support...
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Scheme 50: Oxidative cyclization of bis-hydroxynaphthyl ether 135 to spiroketal 136 using PIDA (15) as an elec...
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Scheme 51: Oxidative spirocyclization of phenolic compound 139 to spirodienone 140 using polymer-supported PID...
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Scheme 52: PIFA-mediated oxidative cyclization of catechol derived substrate 142 to spirocyclic product 143.
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Scheme 53: Oxidative spirocyclization of p-substituted phenolic substrate 145 to aculeatin A (146a) and aculea...
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Scheme 54: Oxidative spirocyclization of p-substituted phenolic substrate 147 to aculeatin A (146a) and aculea...
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Scheme 55: Oxidative spirocyclization of p-substituted phenolic substrate 148 to aculeatin D (149) using elect...
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Scheme 56: Cyclization of phenolic substrate 131 to spirocyclic product 133 using polymer-supported PIFA 150.
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Scheme 57: Iodine(III)-mediated oxidative intermolecular spirocyclization of 7-methoxy-α-naphthol (152) to spi...
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Scheme 58: Oxidative cyclization of phenols 155 to spiro-ketals 156 using electrophilic species PIDA (15).
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Scheme 59: Iodine(III)-catalyzed oxidative spirocyclization of ortho-substituted phenols 158 to spirocyclic ke...
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- Published 18 Jul 2018
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Figure 1: The structures of hypervalent iodine (III) reagents [8].
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Scheme 1: Hypervalent iodine(III)-catalyzed functionalization of alkenes.
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Scheme 2: Catalytic sulfonyloxylactonization of alkenoic acids [43].
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Scheme 3: Catalytic diacetoxylation of alkenes [46].
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Scheme 4: Intramolecular asymmetric dioxygenation of alkenes [48,50].
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Scheme 5: Intermolecular asymmetric diacetoxylation of styrenes [52].
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Scheme 6: Diacetoxylation of alkenes with ester groups containing catalysts 17 [55].
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Scheme 7: Intramolecular diamination of alkenes [56].
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Scheme 8: Intramolecular asymmetric diamination of alkenes [57].
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Scheme 9: Intermolecular asymmetric diamination of alkenes [58].
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Scheme 10: Iodoarene-catalyzed aminofluorination of alkenes [60,61].
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Scheme 11: Iodoarene-catalyzed aminofluorination of alkenes [62].
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Scheme 12: Catalytic difluorination of alkenes with Selectfluor [63].
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Scheme 13: Iodoarene-catalyzed 1,2-difluorination of alkenes [64].
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Scheme 14: Iodoarene-catalyzed asymmetric fluorination of styrenes [64,65].
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Scheme 15: Gem-difluorination of styrenes [67].
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Scheme 16: Asymmetric gem-difluorination of cinnamic acid derivatives [68].
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Scheme 17: Oxyarylation of alkenes [71].
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Scheme 18: Asymmetric oxidative rearrangements of alkenes [72].
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Scheme 19: Bromolactonization of alkenes [75].
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Scheme 20: Bromination of alkenes [77,78].
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Scheme 21: Cooperative strategy for the carbonylation of alkenes [79].
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- Published 20 Jul 2018
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Scheme 1: Previously reported preparation of IBS (1) [17].
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Scheme 2: Oxidation of 2-iodobenzenesulfonate 5 by Oxone in water.
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Figure 1: X-ray structure of an independent crystal unit of IBS 6-K.
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Figure 2: Simplified representation of structure 6-K. Selected interatomic distances (Å): I(1)=O(1) 1.79; I(1...
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Scheme 3: Comparison of the oxidation of sodium 2-iodobenzenesulfonate (5) with NaIO4 and 2-iodobenzenesulfon...
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Scheme 1: Difunctionalization of double C=C bond with the formation of C–O and C–I bonds.
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Scheme 2: Iodo-oxyimidation of styrenes 1a–k with preparation of products 3aa–ka, 3ab–db, 3fb, 3hb, and 3kb.
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Figure 1: Scope of the iodo-oxyimidation of vinylarenes with I2/PhI(OAc)2 system. Reaction conditions: vinyla...
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Figure 2: Molecular structure of 3ca. Atoms are presented as anisotropic displacement parameters (ADP) ellips...
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Scheme 3: The proposed mechanism of iodo-oxyimidation of styrene (1a) using the NHPI/I2/PhI(OAc)2 system with...
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Figure 3: CV curves of styrene (1a, purple), NHPI (2a, red), I2 (blue) and PhI(OAc)2 (green) in 0.1 M n-Bu4NBF...
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Scheme 4: Gram-scale synthesis of compound 3aa.
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Scheme 5: Synthetic utility of the iodo-oxyimides 3aa and 3ab.
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Figure 1: Tautomerism in iodine-based group-transfer reagents probed by 17O NMR spectroscopy (A) and key stru...
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Figure 2: Assignment of acyclic (b) and cyclic (a) structures to 5 and 6, respectively, based on computed iso...
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Figure 3: Protonation of 4a with trifluoroacetic acid (5 equiv) affords 4c, followed by 17O NMR spectroscopy.
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Figure 1: a) Explosion was observed when an arylamine was mixed with aldehydes in the presence of IBX. b) Ben...
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Figure 2: Comparison of the current work with the existing literature reports.
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Figure 3: Synthesis of quinazolin-4(3H)-one derivatives from the reaction of 1 with liquid aldehydes. aYields...
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Figure 4: Synthesis of quinazolin-4(3H)-one derivatives from reaction of 1 and solid aldehydes. aYields with ...
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Figure 5: Crystal structure of 3a (CCDC No. 1823611).
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Figure 6: Plausible mechanism for the quinazolin-4(3H)-ones synthesis using IBX.
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Scheme 1: Large scale synthesis of 3a.
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