Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate. (9th October 2017)

• Record Type: Journal Article
• Authors: Wang, Cheng‐Qiang; Zhang, Yu; Feng, Chao
• Is Part Of: Angewandte Chemie. Volume 129:Number 47(2017)
• Page Start: 15114
• Page End: 15118
• Publication Date: 2017-10-09
• Subjects: C-H-Aktivierung -- Fluoreffekte -- Hydroarylierungen -- Lossen-Umlagerung -- Rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201708505
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: An unprecedented rhodium(III)‐catalyzed hydroarylation of α, α‐difluoromethylene alkynes with N ‐pivaloxyl aroylamides through sequential C−H activation and aryl migration is detailed herein. A large array of α, α‐difluoromethylene alkynes and N ‐pivaloxyl aryl amides were amenable to this transformation, thus providing a novel synthetic protocol for the construction of difluorinated 2‐alkenyl aniline derivatives in high yields and with excellent regioselectivity. Notably, unique fluorine effects were found to underlie the thus unconventional reaction manifold.