Metal-Free Transamidation of Secondary Amides by N-C Cleavage

Transamidation reactions represent a fundamental chemical process involving conversion of one amide functional group into another. Herein, we report a facile, highly chemoselective method for transamidation of N-tert-butoxycarbonylation (N-Boc) activated secondary amides that proceeds under exceedin...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 84; no. 18; pp. 12091 - 12100
Main Authors: Rahman, Md. Mahbubur, Li, Guangchen, Szostak, Michal
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 20.09.2019
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MILD
PHTHALIMIDES
ACTIVATION
HYDROGENATION
REAGENTS
AMINES
CONVERSION
CATALYZED TRANSAMIDATION
ISSN:0022-3263, 1520-6904, 1520-6904
Online Access:Get more information
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Summary:Transamidation reactions represent a fundamental chemical process involving conversion of one amide functional group into another. Herein, we report a facile, highly chemoselective method for transamidation of N-tert-butoxycarbonylation (N-Boc) activated secondary amides that proceeds under exceedingly mild conditions in the absence of any additives. Because this reaction is performed in the absence of metals, oxidants, or reductants, the reaction tolerates a large number of useful functionalities. The reaction is compatible with diverse amides and nucleophilic amines, affording the transamidation products in excellent yields through direct nucleophilic addition to the amide bond. The utility of this methodology is highlighted in the synthesis of Tigan, a commercial antiemetic, directly from the amide bond. We expect that this new metal-free transamidation will have broad implications for the development of new transformations involving direct nucleophilic addition to the amide bond as a key step.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.9b02013