Direct N–H/α,α,β,β-C(sp3)–H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles†,10.1039/C6CC08996H

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Direct N–H/α,α,β,β-C(sp3)–H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles†

Yanlong Du,Aimin Yu,Jiru Jia,Youquan Zhang,Xiangtai Meng

Chemical Communications Pub Date : 01/09/2017 00:00:00 , DOI:10.1039/C6CC08996H

Abstract

A protocol for the direct functionalization of N–H/α,α,β,β-C(sp³)–H of piperidine without any metal or external oxidants is reported. This reaction is promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This is a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties.