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A General Method for the One-Pot Reductive Functionalization of Secondary Amides

Pei-Qiang Huang*, Ying-Hong Huang, Kai-Jiong Xiao, Yu Wang and Xiao-Er Xia

*College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China, Email: pqhuangxmu.edu.cn

P.-Q. Huang, Y.-H. Huang, K.-J. Xiao, Y. Wang, X.-E. Xia, J. Org. Chem., 2015, 80, 2861-2868.

DOI: 10.1021/jo502929x (free Supporting Information)


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Abstract

A one-pot reaction for the transformation of common secondary amides into amines with C-C bond formation consists of in situ amide activation with Tf2O followed by partial reduction and addition of C-nucleophiles. The method is general in scope and allows the use of both hard nucleophiles (RMgX, RLi) and soft nucleophiles, as well as enolates. With soft nucleophiles the presence of ester, cyano, nitro, and tertiary amide groups are tolerated.


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Key Words

alkylamines, propargylamines, triethylsilane


ID: J42-Y2015