Copper(I)-Catalyzed Asymmetric α-Selenenylation of 2-Acylimidazoles

JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 578 - 585

Published: Jan. 21, 2025

A general method for the catalytic asymmetric α-selenenylation of simple carbonyl compounds is lacking. Herein, a copper(I)-catalyzed enantioselective 2-acylimidazoles with electrophilic selenosulfonates uncovered. The reaction enjoys advantages mild conditions, easy protocol, and broad substrate scopes on both selenosulfonates. Mechanistic studies reveal pincer Cu(I)-(S,S)-Ph-BOPA complex as active catalyst. Some traditional selenenylation reagents, such PhSeCl, PhSeSePh, 2-(phenylselanyl)isoindoline-1,3-dione lead to inferior results in terms yield enantioselectivity, highlighting superiority Finally, several transformations based 2-acylimidazole group selenoether are successfully carried out, demonstrating synthetic utilities present methodology.

Language: Английский

Light-Induced 1,3-Thiosulfonylation of β,γ-Unsaturated Ketones with Thiosulfonates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6798 - 6802

Published: Aug. 7, 2024

Sulfur-containing compounds exhibit potent significance in drug molecules. Thiosulfonates as 1,3-thiosulfonylation reactants to olefins have yet be investigated. Herein, we report photoinduced 1,3-difunctionalization of β,γ-unsaturated ketones with thiosulfonates, which undergo a radical 1,2-acyl shift. The protocol features mild conditions, high regioselectivity, and 100% atom economy.

Language: Английский