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

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.

SUBMITTER: Pal A

PROVIDER: S-EPMC6648369 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Pal Arpan A Hussaini Syed Raziullah SR

ACS omega 20190104 1

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 catalyze ...[more]

PMID: 31459329

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