Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes
Beilstein J. Org. Chem. 2010, 6, 1167–1173. doi:10.3762/bjoc.6.133
Supporting Information
Full experimental procedures and spectral data for the new compounds, detailed crystallographic analysis of [(p-cymene)Ru(μ-Cl)3RuCl2(PCy3)] (7), and a cif file with crystallographic data for complex 7.
| Supporting Information File 1: Experimental procedures and spectral data. | ||
| Format: PDF | Size: 92.4 KB | Download |
| Supporting Information File 2: Detailed crystallographic analysis of complex 7. | ||
| Format: PDF | Size: 442.6 KB | Download |
| Supporting Information File 3: X-ray crystal data for complex 7. | ||
| Format: CIF | Size: 63.1 KB | Download |
References
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Figure 1: (a) Structure of universal nova tag resin, (b) structure of H-L-Cys(Trt)-2-ClTrt resin.
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Figure 2: (a) PSMA targeted DUPA rhodamine B chelating conjugate 13. (b) Folate receptor targeted pteroate rh...
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Scheme 1: Synthesis of PSMA tris(tert-butoxy) protected DUPA ligand 4. Reagents and conditions: (a) Triphosge...
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Scheme 2: Attempted synthesis of PSMA targeted DUPA rhodamine B chelating conjugate 13 using Fmoc-Lys(Mtt/Mmt...
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Scheme 3: Synthesis of PSMA targeting DUPA rhodamine B chelating conjugate 13. Reagents and conditions: (a) F...
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Scheme 4: Synthesis of folate receptor targeting pteroate rhodamine B chelating conjugate 17. Reagents and co...
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Figure 3: (i) and (ix) DIC image of LNCaP cells (PSMA+); (ii) binding and internalization of DUPA-rhodamine B...
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Figure 1: A) Overview of LuxI/LuxR-type QS. The LuxI-type protein produces the AHL signal. The AHL diffuses o...
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Figure 2: Overview of SdiA agonism and antagonism single-point screening results in the S. Typhimurium report...
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Figure 3: Chemical structures of the most potent SdiA agonists. Compound names (except for 11-Az) match those...
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Figure 4: Chemical structures of the most potent SdiA antagonists. Compound names preceded by letters match t...
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Figure 5: Dose–response activity curves for OOHL (2) in competition against various concentrations of synthet...
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Figure 1: NDH-2 is a validated target for 1 with an MIC of 1.1 µg/mL against M. tuberculosis.
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Scheme 1: Synthesis of phenothiazine-PEG-amine component.
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Scheme 2: Synthesis of the azotochelin siderophore component.
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Scheme 3: Final conjugation and deprotection to yield a phenothiazine siderophore conjugate.
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Figure 1: The four quorum sensing systems in P. aeruginosa las, iqs, rhl, and pqs. Abbreviations: OdDHL, N-(3...
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Figure 2: Schematic overview of the PQS biosynthesis and involvement of related metabolites and PqsE in virul...
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Figure 3: Anthranilic acid (1) and derivatives thereof (2–4).
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Figure 4: Crystal structure of 6-FABA-AMP in complex with PqsA.
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Figure 5: Structures of substrate mimetic PqsA inhibitors.
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Figure 6: Structures and characteristics of prominent classes of PqsD inhibitors.
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Figure 7: Comparison of docking poses of three prototypic PqsD inhibitors: benzamidobenzoic acid derivative 12...
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Figure 8: Structures and characteristics of hits against PqsD identified through different methods.
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Figure 9: HHQ and PQS analogues as PqsD inhibitors and chemical probe used for screening.
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Figure 10: Structure of PqsD-targeting biofilm inhibitor derived from linezolid.
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Figure 11: Fragment-based PqsE-inhibitors 24–26.
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Figure 12: PqsE co-crystal structures. (A) native product 2-ABA; (B–D) hit fragments 24–26.
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Figure 13: Structurally diverse PqsBC-inhibitors 27–30.
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Figure 14: Native PqsR ligand HHQ (31) which is converted into PQS (32) by PqsH and synthetic inhibitors 33 an...
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Figure 15: Quinazolinone inhibitor 36 (QZN).
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Figure 16: Crystal structure of QZN (36) in complex with PqsRCBD.
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Figure 17: Structures of best fitting compounds 37–40 obtained from docking studies.
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Figure 18: Initial hit 21 and optimized compound 42 (M64).
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Figure 19: Co-crystal structure of M64 (42) with PqsRLBD.
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Figure 20: M64 (42) as the starting point for further optimization leading to 43, which was further modified a...
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Figure 21: Hit fragments from the benzamide (47–48) and oxadiazole class (49–51).
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Figure 22: Structures of dual inhibitors 52–55.
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Figure 23: Sulfonyl pyrimidines 56–58 acting as dual PqsD/PqsR inhibitors.
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- Letter
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Scheme 1: C–H/C–Li cross-coupling reactions of 2H-imidazole 1-oxides 1a–d and carboranyl lithium 2. The react...
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Figure 1: The 1H NMR spectra of 1-(5-(4-bromophenyl)-2-ethyl-2-methyl-2H-imidazol-4-yl)-1,2-dicarba-closo-dod...
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Figure 2: Fragment of the 2D 1H–13C{1H} HSQC (a) and HMBC (b) spectra of imidazolyl carborane 5d in CDCl3 at ...
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Figure 3: Molecular structure of 5d. Selected bond distances (Å) and angles (deg) for molecule 1: C(3)–C(14),...
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Figure 1: Mannosides as inhibitors of the lectin FimH from uropathogenic Escherichia coli.
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Figure 2: Galactosides targeting uropathogenic Escherichia coli FmlH (compounds 8 and 9) and Pseudomonas aeru...
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Figure 3: Mannosides and fucosides as inhibitors of P. aeruginosa LecB.
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Figure 4: β-Cyclodextrin-based antitoxin 19 against S. aureus α-hemolysin and the decavalent Shiga toxin inhi...
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Figure 5: The mechanism of quorum sensing and representative signaling molecules.
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Figure 6: Inhibitors of bacterial quorum sensing.
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Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides
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Scheme 1: Preparation of α-C-acylated β-enamino amides 3 and 4. Reagents and conditions: 2, NMM, EtOCOCl, CH2...
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Scheme 2: Domino fragmentation of 3 to β-keto amides 5 with competing cyclisation to pyrrolin-4-ones 6. Reage...
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Scheme 3: Proposed mechanism for the formation of side products 6.
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Scheme 4: Proposed mechanism for the formation of the target β-keto amides 5.
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Scheme 5: Reactivity of analogues 9, lacking the auxiliary amino group [34].
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Scheme 6: Domino fragmentation of compounds 4 (R2 = R3 = H) to N-protected ω-amino-β-keto amides 11.
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Scheme 7: Ring–chain tautomerism in compounds 11b,c,f,j (n = 2) and reduction to the corresponding β-hydroxy ...
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Figure 1: Previous synthetic approaches to 3a-substituted cis-hydrindan-2,4-diones.
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Scheme 1: Decahydroquinoline 1 as a versatile building block for Lycopodium alkaloid synthesis.
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Figure 2: Examples of Lycopodium alkaloids synthesized from 3a-substituted hydrindan-2,4-diones.
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Scheme 2: A de novo approach to 3a-substituted cis-hydrindan-2,4-diones.
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Scheme 3: Synthesis of enone 4 and the Danheiser annulation. The depicted compounds are all racemic.
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Scheme 4: Transformation of the vinylsilane moiety to ketone 8.
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Figure 3: Stereoview of cis-hydrindane 8.
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Scheme 1: Multistep synthesis of steroidal β-ketoesters 4 and 4' from pregnenolone acetate (1) and pregnadien...
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Scheme 2: Cyclization of compound 4 with hydrazine hydrate (5a), phenylhydrazine (5b) and methylhydrazine (5c...
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Figure 1: 1H NMR spectra of compound 7f in CDCl3 (top; # solvent signal) and in DMSO-d6 (bottom; # solvent si...
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Figure 1: Graphic representation of the bacterial adherence to inert substrata (A) and biofilms developed aft...
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Figure 2: Graphic representation of the adherence index to cellular substrata of PAO1 strain treated with 20 ...
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Figure 3: Fluorescence microscopy images of QSSMs treated euckariote cells, revealing attachment patterns. (C...
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Figure 4: Flow cytometry assays for inflammatory (IL-1β, IL-6), and adhesion markers (ICAM-1, PECAM-1, P-sele...
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Figure 5: Expression levels (fold change) in qRT-PCR experiments for IL-1β, IL-6, TNFα, TGFβ, eNOS, VE-cadher...
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Scheme 1: Synthesis of 2-quinolones 2 through intramolecular Friedel–Crafts hydroarylation of N-aryl propargy...
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Scheme 2: Strategy towards 2-quinolones 8 bearing a branched substituent on the nitrogen atom.
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Figure 1: Scope of the protocol.
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- Published 04 Oct 2018
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Figure 1: Protonated (or organylated) carbonyl (1) and hydroxy (or organyloxy) carbenium ion (2): two possibl...
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Scheme 1: Acid-catalyzed interconversion of carbonyls, hydrates, hemiacetals and acetals.
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Figure 2: Oxacarbenium, oxocarbenium, oxycarbenium and carboxonium ions.
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Figure 1: (a) Structure and (b) reactivity of B12.
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Figure 2: (a) Schematic representation of B12 enzyme-involving systems. (b) Construction of biomimetic and bi...
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Scheme 1: (a) Carbon-skeleton rearrangement mediated by a coenzyme B12-depenedent enzyme. (b) Electrochemical...
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Scheme 2: Electrochemical carbon-skeleton arrangements mediated by B12 model complexes.
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Figure 3: Key electrochemical reactivity of 1 and 2 in methylated forms.
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Scheme 3: Carbon-skeleton arrangements mediated by B12-vesicle artificial enzymes.
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Scheme 4: Carbon-skeleton arrangements mediated by B12-HSA artificial enzymes.
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Scheme 5: Photochemical carbon-skeleton arrangements mediated by B12-Ru@MOF.
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Scheme 6: (a) Methyl transfer reaction mediated by B12-dependent methionine synthase. (b) Methyl transfer rea...
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Scheme 7: Methyl transfer reaction for the detoxification of inorganic arsenics.
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Scheme 8: (a) Dechlorination of 1,1,2,2-tetrarchloroethene mediated by a reductive dehalogenase. (b) Electroc...
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Scheme 9: Visible-light-driven dechlorination of DDT using 1 in the presence of photosensitizers.
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Scheme 10: 1,2-Migration of a phenyl group mediated by the visible-light-driven catalytic system composed of 1...
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Scheme 11: Ring-expansion reactions mediated by the B12-TiO2 hybrid catalyst with UV-light irradiation.
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Scheme 12: Trifluoromethylation and perfluoroalkylation of aromatic compounds achieved through electrolysis wi...
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Figure 1: Design of the target compounds.
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Scheme 1: Synthesis of 3-aminocoumarin-N-benzylpyridinium salts.
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Figure 2: Docked conformations of donepezil (ball-and-stick model; pink), compounds 9a, 9b, 9e, 9h, and 9i (s...
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Figure 3: Binding interactions in the rhAChE binding pocket with (a) 4a, (b) 9a, (c) 9b, (d) 9e, (e) 9h, (f) ...
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Figure 1: Various alkaloids containing propellane frame work.
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Scheme 1: Synthesis of the star-shaped norbornene derivative 11 via trimerization.
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Figure 2: Selected list of ruthenium-based catalysts used for ROM.
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Scheme 2: Synthesis of the C3-symmetric molecule 15 bearing propellane moieties via trimerization and RCM.
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Scheme 3: Synthesis of C3-symmetric molecule 21 bearing propellane moieties via trimerization and RCM.
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Figure 1: Investigational non-catalytic HIV-1 Integrase inhibitors.
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Scheme 1: Boehringer Ingelheim retrosynthesis of quinoline 1.
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Scheme 2: Quinoline ring condensation strategies.
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Scheme 3: Isatoic anhydrides from anthranilic acids with triphosgene.
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Scheme 4: Substituted 2-methyl-4-hydroxyquinolines from isatoic anhydrides and ethyl acetoacetate.
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Scheme 5: Mechanistic hypothesis for the cyclocondensation reaction.
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Scheme 6: Quinoline synthesis with ethyl acetylpyruvate.
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Scheme 7: Elaboration of the benzoic acid ethyl ester to the acetic acid residue.
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Scheme 8: Umpolung addition of ethoxycarbonyl via a MAC strategy.
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Figure 1: Selected examples of sulfenylated heterocycles used in pharmaceuticals and material chemistry.
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Scheme 1: Synthetic routes to organosulfur compounds.
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Scheme 2: Aryl sulfide synthesis.
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Scheme 3: Substrate scope for arylthiol syntheses. The reaction was performed with 1a–g (0.1 mmol) and 2a–d (...
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Figure 2: Crystal structures of compounds 3a, 3d, 3e and 3i.
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Scheme 4: Radical trapping experiments.
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Figure 3: (a) Changes in the fluorescence spectra (in this case intensity, λEx = 455 nm) of [Ir(dF(CF3)ppy)2(...
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Scheme 5: Proposed mechanism for visible light mediated direct C–H sulfenylation.
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Figure 4: Black line: UV–vis spectrum of the degassed [Ir] + 1,3,5-TMB mixture (solution A) in ACN. Blue and ...
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Figure 1: N-Aryl-3,4-dihydroquinazolines 1.
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Scheme 1: Synthetic pathway leading to N-aryl-3,4-dihydroquinazolines 1.
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Scheme 2: Synthesis of compounds 2.
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Figure 2: Reaction intermediate in the synthesis of compound 2a.
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Scheme 3: Addition–elimination mechanism for the heterocyclization.
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Scheme 4: Proposed mechanism involving an intermediate nitrilium ion.
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Figure 1: Schematic structure of Dau-conjugated GnRH-III or its derivatives containing 4Lys with acetyl or bu...
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Figure 2: Cellular uptake of Dau–GnRH-III conjugates and free daunorubicin (Dau) by A2058 cells. Cellular upt...
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Figure 3: Short-term growth inhibitory effects of the conjugates and daunorubicin (Dau) on A2058 cells. The m...
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Figure 4: Effects of conjugates and daunorubicin (Dau) on cell cycle progression of A2058 melanoma cells. The...
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Figure 5: Effects of the conjugates and daunorubicin (Dau) on melanoma cell adhesion. The Delta CI (Delta Cel...
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Figure 6: Chemotactic effects of Dau–GnRH-III conjugates on A2058 cell line. The ‘Chemotaxis index’ (Chtx. in...
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Figure 7: Effects of GnRH-III(Dau=Aoa) (a–c), [4Lys(Ac)]-GnRH-III(Dau=Aoa) (d–f) and [4Lys(Bu)]-GnRH-III(Dau=...
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Figure 8: Schematic representation of the proposed mechanisms of the effects of GnRH-III conjugates containin...
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- Published 25 Sep 2018
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Figure 1: Examples of calix[n]arenes 1 and calix[4]azulenes 2–5.
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Figure 2: Three major computed conformers of OPC4A; a: 1,2-alternate; b: cone and c: saddle.
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Figure 3: Geometry-optimized (ωB97xD/6-31G(d)) and (ωB97xD/GenECP) structures, respectively, computed for lef...
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- Published 24 Sep 2018
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Figure 1: Structures of leopolic acid A and compound 1.
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Scheme 1: Synthesis of 3-decyltetramic intermediate 13. Reagent and conditions: a) TEA, THF, 0 °C to rt, 2.5 ...
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Scheme 2: Synthesis of dipeptide L-Phe-L-Val intermediate 20. Reagents and conditions: a) PTSA·H2O, benzyl al...
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Scheme 3: Synthesis of compound 1. Reagents and conditions: a) n-BuLi, THF, −60 °C, 220 min, 60%; b) H2, Pd/C...
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Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps
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- Published 21 Sep 2018
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Figure 1: Various catalysts used for metathesis reactions.
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Scheme 1: SM coupling and RCM protocol to substituted indene derivative 10.
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Scheme 2: Synthesis of polycycles via SM and RCM approach.
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Figure 2: Various angucyclines.
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Scheme 3: SM coupling and RCM protocol to the benz[a]anthracene skeleton 26.
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Scheme 4: Synthesis of substituted spirocycles via RCM and SM sequence.
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Scheme 5: Synthesis of highly functionalized bis-spirocyclic derivative 37.
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Scheme 6: Synthesis of spirofluorene derivatives via RCM and SM coupling sequence.
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Scheme 7: Synthesis of truxene derivatives via RCM and SM coupling.
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Scheme 8: Synthesis of substituted isoquinoline derivative via SM and RCM protocol.
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Scheme 9: Synthesis to 8-aryl substituted coumarin 64 via RCM and SM sequence.
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Scheme 10: Synthesis of cyclic sulfoximine 70 via SM and RCM as key steps.
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Scheme 11: Synthesis of 1-benzazepine derivative 75 via SM and RCM as key steps.
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Scheme 12: Synthesis of naphthoxepine derivative 79 via RCM followed by SM coupling.
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Scheme 13: Sequential CM and SM coupling approach to Z-stilbene derivative 85.
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Scheme 14: Synthesis of substituted trans-stilbene derivatives via SM coupling and RCM.
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Scheme 15: Synthesis of biaryl derivatives via sequential EM, DA followed by SM coupling.
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Scheme 16: Synthesis of the dibenzocyclooctadiene core of schisandrene.
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Scheme 17: Synthesis of cyclophane 115 via SM coupling and RCM as key steps.
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Scheme 18: Synthesis of cyclophane 120 and 122 via SM coupling and RCM as key steps.
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Scheme 19: Synthesis of cyclophanes via SM and RCM.
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Scheme 20: Synthesis of MK-6325 (141) via RCM and SM coupling.
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- Full Research Paper
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Figure 1: Bicyclic eunicellane-type diterpenes.
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Figure 2: Synthetic eunicellane-type compounds with benzene partial structure.
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Scheme 1: Access to ketoester 14 that did not cyclize to the ethyl vinyl ether under McMurry conditions.
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Scheme 2: Synthesis of the 1,3-cyclohexadiene-containing eunicellane-type [8.4.0]bicycle 18 by McMurry coupli...
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Figure 3: Preferred conformations of diastereomeric diols 18 and 19 including decisive NOESY correlations.
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Scheme 3: Assembly of the envisaged cyclization precursor 27.
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Scheme 4: Structure analysis of diastereomeric cyanohydrins 29 and 30.
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Scheme 5: Formation of allenes 32 and 34 from sterically crowded propargylic alcohol 31.
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Scheme 1: Optimization of the Co-catalyzed carboxylation of 1a.
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Scheme 2: Co-catalyzed carboxylation of propargyl acetates 1.
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Scheme 3: Plausible reaction mechanism for the Co-catalyzed carboxylation of propargyl acetates 1.
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Scheme 4: Optimization of the Co-catalyzed carboxylation of 3a.
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Scheme 5: Co-catalyzed carboxylation of vinyl triflates 3.
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Scheme 6: Co-catalyzed carboxylation of a sterically hindered aryl triflate 5.
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Scheme 7: Optimization of the Co-catalyzed carboxylation of 7a.
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Scheme 8: Scope of the reductive carboxylation of α,β-unsaturated nitriles 7.
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Scheme 9: Scope of the carboxylation of α,β-unsaturated carboxamides 9.
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Scheme 10: Optimization of the Co-catalyzed carboxylation of 11a.
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Scheme 11: Scope of the carboxylation of allylarenes 11.
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Scheme 12: Scope of the carboxylation of 1,4-diene derivatives 14.
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Scheme 13: Plausible reaction mechanism for the Co-catalyzed C(sp3)–H carboxylation of allylarenes.
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Scheme 14: Optimization of the Co-catalyzed carboxyzincation of 16a.
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Scheme 15: Derivatization of the carboxyzincated product.
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Scheme 16: Co-catalyzed carboxyzincation of alkynes 16.
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Scheme 17: Plausible reaction mechanism for the Co-catalyzed carboxyzincation of alkynes 16.
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Scheme 18: Co-catalyzed four-component coupling of alkynes 16, acrylates 18, CO2, and zinc.
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Scheme 19: Proposed reaction mechanism for the Co-catalyzed four-component coupling.
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Scheme 20: Visible-light-driven hydrocarboxylation of alkynes.
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Scheme 21: Visible-light-driven synthesis of γ-hydroxybutenolides from ortho-ester-substituted aryl alkynes.
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Scheme 22: One-pot synthesis of coumarines and 2-quinolones via hydrocarboxylation/alkyne isomerization/cycliz...
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Scheme 23: Proposed reaction mechanism for the Co-catalyzed carboxylative cyclization of ortho-substituted aro...
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Scheme 24: Rh-catalyzed carboxylation of arylboronic esters 25.
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Scheme 25: Rh-catalyzed carboxylation of alkenylboronic esters 27.
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Scheme 26: Plausible reaction mechanism for the Rh-catalyzed carboxylation of arylboronic esters 25.
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Scheme 27: Ligand effect on the Rh-catalyzed carboxylation of 2-phenylpyridine 29a.
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Scheme 28: Rh-catalyzed chelation-assisted C(sp2)–H bond carboxylation with CO2.
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Scheme 29: Reaction mechanism for the Rh-catalyzed C(sp2)–H carboxylation of 2-pyridylarenes 29.
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Scheme 30: Carboxylation of C(sp2)–H bond with CO2.
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Scheme 31: Carboxylation of C(sp2)–H bond with CO2.
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Scheme 32: Reaction mechanism for the Rh-catalyzed C(sp2)–H carboxylation of 2-arylphenols 34.
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Scheme 33: Hydrocarboxylation of styrene derivatives with CO2.
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Scheme 34: Hydrocarboxylation of α,β-unsaturated esters with CO2.
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Scheme 35: Asymmetric hydrocarboxylation of α,β-unsaturated esters with CO2.
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Scheme 36: Proposed reaction mechanism for the Rh-catalyzed hydrocarboxylation of C–C double bonds with CO2.
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Scheme 37: Visible-light-driven hydrocarboxylation with CO2.
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Scheme 38: Visible-light-driven Rh-catalyzed hydrocarboxylation of C–C double bonds with CO2.
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Scheme 39: Optimization of reaction conditions on the Rh-catalyzed [2 + 2 + 2] cycloaddition of diyne 42a and ...
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Scheme 40: [2 + 2 + 2] Cycloaddition of diyne and CO2.
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Scheme 41: Proposed reaction pathways for the Rh-catalyzed [2 + 2 + 2] cycloaddition of diyne and CO2.
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Figure 1: Selected homogeneous catalysts for alkyne metathesis.
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Scheme 1: Synthesis of alkylidyne complex V from bimetallic [(t-BuO)3W≡W(Ot-Bu)3]; the catalytically active d...
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Scheme 2: Synthesis of hexakis(fluoroalkoxide) dimers Mo2F6 [73] and W2F3.
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Figure 2: Molecular structure of W2F3·NHMe2 with thermal displacement parameters drawn at 50% probability. Hy...
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Scheme 3: Preparation of the alkylidyne complex WPhF3.
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Figure 3: Molecular structure of WPhF3 with thermal displacement parameters drawn at 50% probability. Hydroge...
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Scheme 4: Self-metathesis of 1-phenyl-1-propyne derivatives by tungsten complexes W2F3 and WPhF3.
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Figure 4: Conversion versus time diagram for the self-metathesis of 1-phenyl-1-propyne catalyzed by 0.5 mol % ...
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