Organic Chemistry Portal

Abstracts

Search:

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.szostakrutgers.edu

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

DOI: 10.1055/s-0039-1690055 (free Supporting Information)


see article for more reactions

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.

see article for more examples



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