Visible-Light-Enabled Oxidative Alkylation of Unactivated Alkenes with Dimethyl Sulfoxide through Concomitant 1,2-Aryl Migration

• DOI: 10.1021/acs.orglett.8b03340
• Publication Date: 2018-11-28T17:30:22Z
• Authors: Maojian Lu; Honggui Qin; Zhaowei Lin; Mingqiang Huang; Wen Weng; Shunyou Cai
• Keywords: Hypervalent molecule; Sulfoxide; Visible spectrum

Metal-free oxidative radical 1,2-alkylarylation of unactivated alkenes with the α-C(sp3)–H bond dimethyl sulfoxide has been developed. This study realizes a new, conceptually novel technology for convenient construction variety α-aryl-γ-methylsulfinyl ketones in good-to-excellent yields synergistic interactions visible light irradiation, organic fluorophores 4CzIPN, and hypervalent iodine(III) reagent under transition-metal free conditions. A remarkable kinetic isotope effect was observed, which helped provide insight into reaction's mechanistic course.