Synthesis

Room-temperature debenzylation of N-benzylcarboxamides by N-bromosuccinimide

L Kuang, J Zhou, S Chen, K Ding

Index: Kuang, Liping; Zhou, Jing; Chen, Sheng; Ding, Ke Synthesis, 2007 , # 20 p. 3129 - 3134

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Citation Number: 9

Abstract

Abstract A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono-or disubstituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism.

~78%

~76%

~82%

~74%

~72%

~87%

~63%

~80%

~76%

~83%

~68%

~64%

~87%

~43%

~90%

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