DMSO as a Switchable Alkylating Agent in Heteroarene C−H Functionalization. Issue 40 (12th June 2018)

• Record Type: Journal Article
• Authors: Garza‐Sanchez, R. Aleyda; Patra, Tuhin; Tlahuext‐Aca, Adrian; Strieth‐Kalthoff, Felix; Glorius, Frank
• Is Part Of: Chemistry. Volume 24:Issue 40(2018)
• Page Start: 10064
• Page End: 10068
• Publication Date: 2018-06-12
• Subjects: C−H functionalization -- heteroarenes -- methylation -- methylthiomethylation -- photoredox catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201802352
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Herein, we report a novel strategy for the activation of DMSO to act as a versatile alkylating agent in heteroarene C−H functionalization. This direct, simple, and mild switch between methylation/trideuteromethylation and methylthiomethylation of heteroarenes was achieved under reagent‐controlled photoredox catalysis conditions. The proposed mechanism is supported by both experimental and computational studies. Abstract : Mild alkylation : A direct, simple, and mild methylation, trideuteromethylation, and methylthiomethylation of heteroarenes using DMSO as an alkylating agent is reported. This novel strategy was achieved under reagent‐controlled photoredox catalysis conditions. The proposed mechanism is supported by both experimental and theoretical studies.