Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts

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

Published: May 2, 2025

The site-selective incorporation of sulfilimine functionalities into aromatic compounds provides a vital strategy for drug discovery in medicinal chemistry. However, green and sustainable methods realizing the goal are still limited. Here, we report copper-catalyzed S-arylation sulfenamides with aryl thianthrenium salts irradiated by visible light without photocatalyst, which exhibited fine functional-group compatibility gave desired products high yields. Mechanistic investigations revealed that key to achieving these results is generation an electron donor-acceptor (EDA) complex between under basic conditions.

Language: Английский

Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates

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

Published: May 20, 2025

We herein disclose a mild metal-free strategy for the construction of heteroaryl-derived sulfilimines. Central to this approach is in situ generated sulfinimidoyl fluoride intermediate that exhibits an optimal balance reactivity and stability efficient S(IV)-derived SuFEx reactions with heteroarenes without Lewis acids or base additives. This protocol enables rapid incorporation broad range afford diverse sulfilimine scaffolds potent antimicrobial activities against plant pathogens.

Language: Английский