Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 4, 2025

A photocatalytic approach for the synthesis of difluorinated glycoamino acids and neoglycopeptides from bromodifluoroacetamides sugar-derived olefins is presented. This method stands out because its simplicity, atomic economy, mild reaction conditions, allowing compatibility with both natural unnatural amino peptides. Additionally, it demonstrates efficacy across a variety carbohydrates, including furanoses, pyranoses, pentose, hexoses, disaccharides, accommodating an extensive range protecting groups, even in their deprotected forms.

Language: Английский

Stereodivergent Construction of Enamides via a Radical-Mediated Isodesmic Reaction

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6749 - 6759

Published: April 10, 2025

Language: Английский

Photoredox-Catalyzed Radical Hydroalkylation of Azobenzenes with Alkylboronic Acids

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

The facile synthesis of N-alkyl-N,N'-diarylhydrazines has been a long-standing challenge. Here, we report photoredox-catalyzed hydroalkylation azobenzenes with alkylboronic acids, which successfully affords diverse N-alkyl-N,N'-diarylhydrazines. With an acridinium salt as the photocatalyst and upon visible light irradiation, broad range acids reacted smoothly in presence Lewis base at ambient temperature. Mechanistic studies revealed that reaction proceeds via generation alkyl radicals is facilitated by photoredox catalysis.

Language: Английский