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

Authors :: Pal A
Hussaini SR
Source :: ACS omega [ACS Omega] 2019 Jan 04; Vol. 4 (1), pp. 269-280. Date of Electronic Publication: 2019 Jan 04 (Print Publication: 2019).
Publication Year :: 2019
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 Rh <subscript>2</subscript> (OAc) <subscript>4</subscript> or Ru(PPh <subscript>3</subscript> ) <subscript>3</subscript> Cl <subscript>2</subscript> catalysts.<br />Competing Interests: The authors declare no competing financial interest.

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