Electrophilic trifluoromethylselenolation of terminal alkynes with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
Beilstein J. Org. Chem. 2017, 13, 2626–2630. doi:10.3762/bjoc.13.260
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- Full Research Paper
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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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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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Figure 1: The tetrasaccharides associated with the pneumonicoccal serogroup 6.
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Figure 2: Retrosynthetic analysis.
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Scheme 1: Preparation of D-glucosyl donor 6. Reaction conditions: a) NapBr/PMBCl, NaH, DMF, rt, 12 h, 90% (6a...
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Scheme 2: Preparation of L-rhamnosyl acceptor 5. Reaction conditions: a) Py, BzCl, rt, 12 h, 99%; b) DDQ, DCM...
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Scheme 3: Preparation of ribitol acceptor 7. Reaction conditions: a) Me2C(OMe)2, pTSA, CH3COCH3, rt, 81%; b) ...
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Scheme 4: Stepwise synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, DCM/Et2O (5:1), 4 Å MS, −3...
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Scheme 5: One-pot synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, 4 Å MS, DCM/Et2O (4:1), N2,...
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- Letter
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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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Figure 1: A figure showing the hydrogen bonding patterns observed in (a) duplex (b) triplex and (c) quadruple...
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Figure 2: (a) Portions of MATα1–MATα2 are shown contacting the minor groove of the DNA substrate. Key arginin...
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Figure 3: Chemical structures of naturally occurring and synthetic hybrid minor groove binders.
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Figure 4: Synthetic structural analogs of distamycin A by replacing one or more pyrrole rings with other hete...
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Figure 5: Pictorial representation of the binding model of pyrrole–imidazole (Py/Im) polyamides based on the ...
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Figure 6: Chemical structures of synthetic “hairpin” pyrrole–imidazole (Py/Im) conjugates.
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Figure 7: (a) Minor groove complex formation between DNA duplex and 8-ring cyclic Py/Im polyamide (conjugate ...
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Figure 8: Telomere-targeting tandem hairpin Py/Im polyamides 23 and 24 capable of recognizing >10 base pairs; ...
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Figure 9: Representative examples of recently developed DNA minor groove binders.
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Figure 10: Chemical structures of bisbenzamidazoles Hoechst 33258 and 33342 and their synthetic structural ana...
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Figure 11: Chemical structures of bisamidines such as diminazene, DAPI, pentamidine and their synthetic struct...
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Figure 12: Representative examples of recently developed bisamidine derivatives.
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Figure 13: Chemical structures of chromomycin, mithramycin and their synthetic structural analogs 91 and 92.
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Figure 14: Chemical structures of well-known naturally occurring DNA binding intercalators.
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Figure 15: Naturally occurring indolocarbazole rebeccamycin and its synthetic analogs.
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Figure 16: Representative examples of naturally occurring and synthetic derivatives of DNA intercalating agent...
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Figure 17: Several recent synthetic varieties of DNA intercalators.
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Figure 18: Aminoglycoside (neomycin)–Hoechst 33258/intercalator conjugates.
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Figure 19: Chemical structures of triazole linked neomycin dimers and neomycin–bisbenzimidazole conjugates.
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Figure 20: Representative examples of naturally occurring and synthetic analogs of DNA binding alkylating agen...
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Figure 21: Chemical structures of naturally occurring and synthetic analogs of pyrrolobenzodiazepines.
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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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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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- 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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- 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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- 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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- 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 07 May 2018
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Scheme 1: Selected transformations with ferrocene/ferrocenium as SET reagents (a) [27], catalyzed (b,c) [29-31] and medi...
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Scheme 2: Methyl esters of ferrocene carboxylic acids 1 [45,46], 2 [47-49], 2a [50], 2b [51,52], 3, 4 [54] and pseudo octahedral high-spin...
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Figure 1: Normalized cyclic voltammograms for anodic sweeps of 1–4 in CH2Cl2/[n-Bu4N][B(C6F5)4] (scan rate 10...
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Figure 2: Electrochemical potentials E1/2 (vs FcH/FcH+) of esters 1–4 versus sum of Hammett values ∑σp/m with...
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Figure 3: a) Partial ATR IR spectra (transmission normalized, C=O stretching vibration region) of solids 1–4....
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Figure 4: IR spectroelectrochemical oxidation of 3 to 3+ in CH2Cl2/[n-Bu4N][B(C6F5)4] (C=O stretching vibrati...
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Figure 5: a) Normalized UV–vis spectra of 1–4 in CH2Cl2. b) Normalized UV–vis absorptions of 1+–4+ in CH2Cl2/[...
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Figure 6: Absorption energy E of ferrocene bands of 1–4 (a) and energies of the low energy absorption maxima ...
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Figure 7: UV–vis spectroelectrochemical oxidation of 3 in CH2Cl2/[n-Bu4N][B(C6F5)4] (0–1.1 V vs Ag pseudo ref...
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Figure 8: 1H NMR oxidation titration of 3 in CD2Cl2 with [N(2,4-C6H3Br2)3]+ as oxidant. a[N(2,4-C6H3Br2)3]. b...
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Scheme 1: Pd-catalyzed aminations at C-2 or C-4 in the 13α-estrone series. Reactions were performed on a 0.25...
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Scheme 2: Two-step synthesis of 2-amino-13α-estra-1,3,5(10)-trien-17-one (13).
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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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Figure 1: Number of two-body, three-body and four-body clusters for systems with up to 13 molecules.
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Figure 2: Water clusters from [23] studied in this work.
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Figure 3: Cyclic-chair structure of the water hexamer.
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Figure 4: Comparison of the structures of the first seven water clusters optimized on the Hartree–Fock and MP...
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Figure 5: Electrostatic and dispersion interaction energy for three different structures of the water dimer. ...
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Figure 6: Two- and three-body dispersion energies for three structures of the water trimer. In all conformati...
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Figure 7: Number of three-body subclusters for which the three-body dispersion energy is attractive (red) or ...
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Figure 8: DFT-SAPT energy decomposition of the three-body interaction energy of the water trimer calculated u...
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Figure 9: DFT-SAPT energy decomposition of the sum of the three- and four-body interaction energy of the wate...
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Figure 10: Sum of three- and four-body dispersion interactions compared to the total many-body interactions Δ3...
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Figure 11: Relative contribution of the two-body dispersion interaction energy to the complete two-body and to...
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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 27 Apr 2018
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Figure 1: Examples of equipment used to perform mechanochemistry on nucleoside and nucleotide substrates (not...
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Figure 2: Ganciclovir.
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Scheme 1: Nucleoside tritylation effected by hand grinding in a heated mortar and pestle.
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Scheme 2: Persilylation of ribonucleoside hydroxy groups (and in situ acylation of cytidine) in a MBM.
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Scheme 3: Nucleoside amine and carboxylic acid Boc protection using an improvised attritor-type mill.
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Scheme 4: Nucleobase Boc protection via transient silylation using an improvised attritor-type mill.
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Scheme 5: Chemoselective N-acylation of an aminonucleoside using LAG in a MBM.
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Scheme 6: Azide–alkyne cycloaddition reactions performed in a copper vessel in a MBM.
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Figure 3: a) Custom-machined copper vessel and zirconia balls used to perform CuAAC reactions (showing: upper...
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Scheme 7: Thiolate displacement reactions of nucleoside derivatives in a MBM.
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Scheme 8: Selenocyanate displacement reactions of nucleoside derivatives in a MBM.
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Scheme 9: Nucleobase glycosidation reactions and subsequent deacetylation performed in a MBM.
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Scheme 10: Regioselective phosphorylation of nicotinamide riboside in a MBM.
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Scheme 11: Preparation of nucleoside phosphoramidites in a MBM using ionic liquid-stabilised chlorophosphorami...
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Scheme 12: Preparation of a nucleoside phosphite triester using LAG in a MBM.
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Scheme 13: Internucleoside phosphate coupling linkages in a MBM.
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Scheme 14: Preparation of ADPR analogues using in a MBM.
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Scheme 15: Synthesis of pyrophosphorothiolate-linked dinucleoside cap analogues in a MBM to effect hydrolytic ...
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Figure 4: Early low temperature mechanised ball mill as described by Mudd et al. – adapted from reference [78].
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Scheme 16: Co-crystal grinding of alkylated nucleobases in an amalgam mill (N.B. no frequency was recorded in ...
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Figure 5: Materials used to prepare a smectic phase.
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Figure 6: Structures of 5-fluorouracil (5FU) and nucleoside analogue prodrugs subject to mechanochemical co-c...
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Scheme 17: Preparation of DNA-SWNT complex in a MBM.
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- Published 26 Apr 2018
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Figure 1: Conventional chemotherapy versus targeted chemotherapy. Black color = Solid malignant tumor; red = ...
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Figure 2: A. General structural architecture of the ideal navigated drug delivery system [31]. B. General structu...
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Figure 3: Binding and penetration mechanism of iRGD. The iRGD peptide is accumulated on the surface of αv int...
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Figure 4: Representative examples of anticancer drugs utilized for the construction of PDCs. The most usual c...
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Figure 5: Illustration of the drug release mechanism from the self-immolative spacer PABC conjugated to a tum...
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Figure 6: Structures of the PDCs named AN-152 and AN-207.
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Figure 7: Structure of the PDC named AN-238.
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Figure 8: Chemical structure and synthetic scheme for the PDC ANG1005. (A) ANG1005 is composed of three molec...
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Figure 9: Structure of oxime linked Dau–GnRH-III conjugate with or without cathepsin B labile spacer and thei...
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Figure 10: Synthesis of the most effective GnRH-III–Dau conjugate with two drug molecules [153].
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Figure 11: Structures of the four different PDCs of D-Lys6-GnRH-I and gemcitabine (GSG, GSG2, 3G, 3G2) [19].
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Figure 12: Structures of (A) native sunitinib; (B) SAN1 analog of sunitinib and (C) assembled PDC named SAN1GS...
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Figure 13: Synthetic scheme for the formation of GSG and the unexpected side product [156].
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Figure 14: Illustration of uncharted guanidinium peptide coupling reagent side reactions during PDCs synthesis ...
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Figure 15: Putative mechanism for the formation of the uronium side product [156].
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- Published 25 Apr 2018
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Figure 1: The conformers of (a) water dimer and (b) HF dimer.
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Figure 2: Schematic representation of strong pair excitations in the framework of the DLPNO-CCSD(T) method. E...
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Figure 3: Dissociation curve of Conf1 of water dimer as a function of the H-bond distance. Its nearly linear ...
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Figure 4: Decomposed HF energy terms (top), and correlation energy terms (bottom) of Conf1 of water dimer as ...
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Figure 5: Comparison of total interaction, electrostatic interaction, and London dispersion energies calculat...
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Figure 1: Schematic synthesis of cyclic KNGRE (A) and XNGRE (B) drug conjugates. a) Mtt-cleavage: 2% TFA/DCM;...
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Figure 2: (A) HT1080 and (B) HT-29 cells. Uptake of conjugate 1 (light green); 2 (red); 3 (light blue); 4 (pi...
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Figure 1: Total ion chromatograms of headspace extracts from A) Aspergillus fischeri NRRL 181, B) Aspergillus...
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Scheme 1: Volatiles from Aspergillus fischeri. For all chiral compounds in Schemes 1–5 the relative configura...
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Scheme 2: Biosynthesis of bisabolanes and related terpenes in A. fischeri.
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Scheme 3: Biosynthesis of daucanes in A. fischeri.
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Scheme 4: Volatiles from A. kawachii. A) Proposed biosynthesis of sesquiterpenes, B) other identified volatil...
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Scheme 5: Volatiles from A. clavatus.
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- Published 23 Apr 2018
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Scheme 1: The Corey–Fuchs reaction.
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Scheme 2: Electrochemical reduction of a carbon–halogen bond.
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Scheme 3: Electrochemical synthesis of vinyl bromides [25].
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Scheme 4: Scope of this work.
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Figure 1: Voltammetric curves of 1a 0.020 mol dm−3; Pt, glassy carbon (GC) or Ag cathode. ν = 0.2 V s−1, T = ...
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Scheme 5: Possible products from the electrolysis of 2-(2,2-dibromovinyl)naphthalene (1a).
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Figure 2: Variation of the amounts of 1a, 2a, and 3a with the number of Faradays of 1a.
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Scheme 6: Mechanistic hypothesis for the synthesis of alkyne 2a and bromoalkyne 3a from 2-(2,2-dibromovinyl)n...
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Scheme 7: Possible reaction using NaClO4 as supporting electrolyte.
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Scheme 8: Electrochemical synthesis of 9-ethyl-3-ethynyl-9H-carbazole (2b).
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Scheme 9: Electrochemical synthesis of 1-ethynyl-4-methoxybenzene (2c).
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- Published 20 Apr 2018
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Figure 1: Representative pyrrolo[3,4-c]pyrrole-1,3-diones and polysubstituted pyrrole derivatives.
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Scheme 1: Synthetic pathway for the preparation of pyrrolo[3,4-c]pyrrole-1,3-diones and highly substituted py...
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Scheme 2: Scope of one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones 12a–k. General reaction conditions: ...
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Scheme 3: Scope of the synthesis of highly substituted pyrrole derivatives 13a–n. General reaction conditions...
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Scheme 4: Synthesis of 13k from 12d and ethylamine.
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Scheme 1: Previously reported post-Ugi-4CR methods for the synthesis of 2-oxindoles and spirocyclic 2-oxindol...
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Scheme 2: Post-Ugi-4CR/transamidation/cyclization sequence.
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Scheme 3: Base-promoted intramolecular 5-endo-dig cyclization.
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Figure 1: ORTEP diagram of compound 7a.
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Figure 2: Readily and synthetically accessible starting materials.
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Scheme 4: Reaction scope with varying combinations of substrates.
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Scheme 5: Synthesis of 5-chloro-1'-phenylspiro[indoline-3,2'-pyrrolidine]-2,5'-dione (8a).
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Figure 3: Small molecule library of spiro[indoline-3,2'-pyrrolidine]-2,5'-dione analogs.
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Scheme 6: Method applicability for the one-pot synthesis of 5-HT6 receptor antagonist 8j [53].
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- Published 17 Apr 2018
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Scheme 1: Synthetic routes of CEPDO and CBPDO.
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Figure 1: Structures and molecular orbitals of (a) CEPDO and (b) CBPDO.
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Figure 2: UV–vis absorption and photoluminescence spectra in DCM solution (1 × 10−5 M and 1 × 10−6 M, respect...
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Figure 3: Cyclic voltammograms for CEPDO and CBPDO in DCM solution.
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Figure 4: DSC and TGA curves of CEPDO and CBPDO.
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