Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
Md. Mahbubur Rahman, Guangchen Li, Michal Szostak*
*Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA,
Email: michal.szostak
rutgers.edu
Md. M. Rahman, G. Li, M. Szostak, Synthesis, 2020, 52, 1060-1066.
DOI: 10.1055/s-0039-1690055
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Abstract
Ground-state destabilization of amides enables an exceedingly mild method for the direct thioesterification and selenoesterification by selective N-C(O) bond cleavage in the absence of transition metals. Acyclic amides undergo N-C(O) to S/Se-C(O) interconversion to give the corresponding thioesters and selenoesters in excellent yields at room temperature via a tetrahedral intermediate pathway.
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Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions
Y. Liu, S. Shi, M. Achtenhagen, R. Liu, M. Szostak, Org. Lett., 2017, 19, 1614-1617.
Key Words
amides, N-C activation, metal-free, thioesters, selenoesters, thioesterification, selenoesterification, tetrahedral intermediates
ID: J66-Y2020
