Amide activation: an emerging tool for chemoselective synthesis

Chemical Society Reviews
Daniel KaiserNuno Maulide

Abstract

It is textbook knowledge that carboxamides benefit from increased stabilisation of the electrophilic carbonyl carbon when compared to other carbonyl and carboxyl derivatives. This results in a considerably reduced reactivity towards nucleophiles. Accordingly, a perception has been developed of amides as significantly less useful functional handles than their ester and acid chloride counterparts. However, a significant body of research on the selective activation of amides to achieve powerful transformations under mild conditions has emerged over the past decades. This review article aims at placing electrophilic amide activation in both a historical context and in that of natural product synthesis, highlighting the synthetic applications and the potential of this approach.

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Citations

Feb 15, 2019·Angewandte Chemie·Derek Yiren OngShunsuke Chiba
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Mar 12, 2020·Organic Letters·Haoqi ZhangNuno Maulide
Aug 19, 2021·Chemical Reviews·Guangrong MengMichal Szostak

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