Amide Activation by Tf₂O: Reduction of Amides to Amines by NaBH₄ under Mild Conditions

Shao-Hua Xiang, Jian Xu, Hong-Qiu Yuan, Pei-Qiang Huang*

*Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China, Email: pqhuangxmu.edu.cn

S.-H. Xiang, J. Xu, H.-Q. Yuan, P.-Q. Huang, Synlett, 2010, 1829-1832.

DOI: 10.1055/s-0030-1258111

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Abstract

An expeditious and practical method for the reduction of various amides and lactams to amines in good to excellent yields is consisted of activation with Tf₂O followed by reduction with sodium borohydride in THF at room temperature. This method offers TBDPS-group tolerance, short reaction time, and a simple workup.

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Key Words

reduction of amides, amines, amide activation, triflic anhydride, sodium borohydride

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ID: J60-Y2010-1910