Tetrabutylammonium iodide-catalyzed oxidative coupling of enamides with sulfonylhydrazides: synthesis of β-keto-sulfones?

Organic & Biomolecular Chemistry Pub Date: 2015-05-19 DOI: 10.1039/C5OB00742A

Abstract

A facile synthetic route towards pharmaceutically interesting β-keto-sulfone derivatives by tetrabutylammonium iodide (TBAI)/tert-butyl hydroperoxide (TBHP) mediated oxidative coupling of readily prepared enamides with economical sulfonylhydrazides is described. The corresponding β-keto-sulfone compounds were obtained in moderate to good yields. The present method is metal-free and base-free and shows tolerance to a variety of functional groups.

Graphical abstract: Tetrabutylammonium iodide-catalyzed oxidative coupling of enamides with sulfonylhydrazides: synthesis of β-keto-sulfones
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