Issue 14, 2019

Employing thiocyanate salts as a nitrogen source via C[triple bond, length as m-dash]N bond cleavage: divergent synthesis of α-ketoamides and 2-acyloxazoles

Abstract

A switchable procedure for the synthesis of α-ketoamides and 2-acyloxazoles from aryl methyl ketones and thiocyanate salts is reported. This work discloses the first example of thiocyanate salts being used as amino surrogates via C[triple bond, length as m-dash]N bond cleavage. This work enriches the applications of thiocyanate salts beyond limited use as ‘SCN’, ‘CN’, or ‘S’ resources. Furthermore, this work opens a fruitful avenue for the synthesis of α-ketoamides and 2-acyloxazoles in a process with additive-controlled chemoselectivity.

Graphical abstract: Employing thiocyanate salts as a nitrogen source via C [[triple bond, length as m-dash]] N bond cleavage: divergent synthesis of α-ketoamides and 2-acyloxazoles

Supplementary files

Article information

Article type
Research Article
Submitted
28 Apr 2019
Accepted
04 Jun 2019
First published
05 Jun 2019

Org. Chem. Front., 2019,6, 2534-2538

Employing thiocyanate salts as a nitrogen source via C[triple bond, length as m-dash]N bond cleavage: divergent synthesis of α-ketoamides and 2-acyloxazoles

C. Wang, X. Geng, P. Zhao, Y. Zhou, Y. Wu and A. Wu, Org. Chem. Front., 2019, 6, 2534 DOI: 10.1039/C9QO00570F

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