Iron‐Catalyzed Intermolecular Azidabenzoyl Difluoromethylation of Alkenes to Access β‐Difluoroacyl Azides. Issue 46 (12th December 2022)

• Record Type: Journal Article
• Authors: Wang, Xia; Fang, Mougui; Wu, Shiguang; Wu, Jingjing; Wu, Fanhong
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-12
• Subjects: alkenes -- β-Difluoroacyl azides -- difluoromethylation -- iron-catalyzed -- radical-mediated; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201213
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A Fe(II)‐catalyzed three‐component reaction of 2‐iodo‐2, 2‐difluoroacetophenones, alkenes and TMSN3 is described, which provides a particularly valuable route to access difluoroalkylated azides with high yields. The method permits the efficient azidation of varied β‐ difluoroacyl‐benzylic radicals in mild conditions with high functional group tolerance. Preliminary mechanistic investigation indicated that a radical‐mediated process was involved in this azidadifluoroacylation reaction. Abstract : We have reported an Fe(II)‐catalyzed three‐component reaction of 2‐iodo‐2, 2‐difluoroacetophenones, alkenes and TMSN3 for the synthesis of difluoroacyl‐substituted azides. The present method offers several advantages including broad substrate scope, good yields of products, and mild reaction condition. Preliminary mechanistic investigation indicated that a radical‐mediated process was involved in this azidadifluoroacylation reaction.