Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions

Nonplanar, electronically destabilized amides have emerged as powerful intermediates in organic synthesis. We report a highly selective method for transamidation of common secondary amides under mild, metal-free conditions that relies on transient N-selective functionalization to weaken amidic reson...

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Bibliographic Details
Published in:	Organic letters Vol. 19; no. 7; p. 1614
Main Authors:	Liu, Yongmei, Shi, Shicheng, Achtenhagen, Marcel, Liu, Ruzhang, Szostak, Michal
Format:	Journal Article
Language:	English
Published:	United States 07.04.2017
ISSN:	1523-7052, 1523-7052
Online Access:	Get more information
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Summary:	Nonplanar, electronically destabilized amides have emerged as powerful intermediates in organic synthesis. We report a highly selective method for transamidation of common secondary amides under mild, metal-free conditions that relies on transient N-selective functionalization to weaken amidic resonance. The combination of rational modification of the amide bond with nucleophilic addition mechanism, and the thermodynamic collapse of the resultant tetrahedral intermediate constitutes a two-step procedure to accomplish a challenging transamidation of secondary amides under mild conditions.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7052 1523-7052
DOI:	10.1021/acs.orglett.7b00429