Metal-Free Transamidation of Secondary Amides via Selective N–C Cleavage under Mild Conditions
- 14 March 2017
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 19 (7), 1614-1617
- https://doi.org/10.1021/acs.orglett.7b00429
Abstract
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.Keywords
Funding Information
- Rutgers, The State University of New Jersey
- National Natural Science Foundation of China (21472161)
- Priority Academic Program Development of Jiangsu Higher Education (BK2013016)
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