Photo‐Mediated Intermolecular Coupling of Alkenes with Ketones via Acyloxy Nitroso Compounds

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(15), P. 8547 - 8551

Published: Feb. 10, 2021

Abstract An atom‐economic intermolecular radical addition reaction of acyloxy nitroso compounds to electron‐deficient alkenes mediated by visible light is reported. The starting derivatives are readily prepared oxidation the corresponding oximes from ketones and overall transformation represents an oxidative coupling a ketone with Michael acceptor. cascade proceeds smoothly under mild conditions, providing series valuable functionalized in moderate good yields. Mechanistic studies suggest that these cascades proceed via addition/coupling processes controlled persistent effect (PRE) NO acting as species.

Language: Английский

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Photoredox‐Catalyst‐Enabled para‐Selective Trifluoromethylation of tert‐Butyl Arylcarbamates

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(35), P. 19030 - 19034

Published: June 23, 2021

Abstract The direct incorporation of a trifluoromethyl group on an aromatic ring using radical pathway has been extensively investigated. However, the highly para ‐selective C−H trifluoromethylation class arenes not achieved. In this study, we report light‐promoted 4,5‐dichlorofluorescein (DCFS)‐enabled arylcarbamates Langlois reagent. preliminary mechanistic study revealed that activated organic photocatalyst coordinated with arylcarbamate led to trifluoromethylation. Ten‐gram scale reaction performs well highlighting synthetic importance new protocol.

Language: Английский

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Highly Selective α-Addition and β-Conjugate Addition Products from Peptides Composed of α,β-Unsaturated γ-Amino Acids

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1549 - 1560

Published: Jan. 23, 2025

β-Addition products are common in conjugate addition reactions consisting of α,β-unsaturated carbonyl compounds. Here, we reporting an uncommon α-addition product as a major the thioacetic acid reaction on peptide (E)-α,β-unsaturated γ-amino acids. In addition, observed highly diastereoselective β-addition from thiophenol and thioethanol peptides. comparison, amides give both α- with only reaction. Further, conformations were studied single crystals well solution. The α-thioacetate (α,γ-disubstituted acid) adopted regular 12-helix conformation, whereas (β,γ-disubstituted slightly distorted conformation. A kink is at site structures all products. Overall, stereospecific reported here can be explored to introduce diverse functional groups backbone.

Language: Английский

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Unveiling a carbazole-based photocatalyst for visible-light-driven synthesis of indolyl diarylmethanes and 2-benzimidazoles

Catalysis Science & Technology, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A carbazole-based photocatalyst (MD) incorporating a dicyanovinyl acceptor and exhibiting superior redox potential has been demonstrated for sustainable photocatalytic approach to synthesize indolyl diarylmethanes 2-substituted benzimidazoles.

Language: Английский

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Benzophenothiazine/Boronic Acid Cooperative Photocatalysis Enables the Synthesis of γ-Lactones via the [3 + 2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Olefins

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4975 - 4983

Published: March 10, 2025

Language: Английский

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