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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
Title: Thioesterification and Selenoesterification of Amides via Selective N–C Cleavage at Room Temperature: N–C(O) to S/Se–C(O) Interconversion
The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles. Herein, we report an exceedingly mild method for the direct thioesterification and selenoesterification of amides 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 (cf. an acyl metal).  more » « less
Award ID(s):
1650766
NSF-PAR ID:
10146167
Author(s) / Creator(s):
; ;
Date Published:
Journal Name:
Synthesis
Volume:
52
Issue:
07
ISSN:
0039-7881
Page Range / eLocation ID:
1060 to 1066
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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