Expedient access to N-alkylphthalimides via redox-neutral photocatalysed Giese-type reactions
1Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical University, No. 888 Yinxian Avenue East, Ningbo 315100, China. jinxp@mail.zjpc.net.cn.
Abstract:
The photoredox-catalysed Giese-type reaction has emerged as a useful and powerful platform for radical-based transformations. Herein, a novel protocol for the preparation of N-alkylphthalimides has been successfully developed via the reactions of N-vinylphthalimides with radicals using alkyl silicates or Hantzsch esters as the radical precursors. According to the result of deuteration experiments, a mechanism involving a radical addition/SET reduction/protonation process has been proposed. The synthetic application of N-alkylphthalimide has also been demonstrated by deprotecting the phthalimido group using the Ing-Manske procedure.
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