Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones

Arpan Pal; Syed Raziullah Hussaini

doi:10.1021/acsomega.8b02633

Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones

ACS Omega. 2019 Jan 4;4(1):269-280. doi: 10.1021/acsomega.8b02633. eCollection 2019 Jan 31.

Authors

Arpan Pal¹, Syed Raziullah Hussaini¹

Affiliation

¹ Department of Chemistry and Biochemistry, The University of Tulsa, 800 S. Tucker Dr., Tulsa, Oklahoma 74104, United States.

Abstract

The coupling of thioamides and donor/acceptor-substituted diazocarbonyl compounds is reported for the first time. The present report provides a mild, catalytic method that couples thioamides and donor/acceptor-substituted diazocarbonyl compounds to form enamino esters and enaminones. Unlike traditional methods for the synthesis of enamino esters and enaminones from thioamides, both N-alkyl thioamides and thiocarbamates are suitable substrates in this coupling reaction. Copper(I) bromide catalyzes the reaction and provides enamino esters and enaminones chemo- and diastereoselectively in less time than Rh₂(OAc)₄ or Ru(PPh₃)₃Cl₂ catalysts.