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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:

Md. M. Rahman, G. Li, M. Szostak, Synthesis, 2020, 52, 1060-1066.

DOI: 10.1055/s-0039-1690055

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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