Palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrene derivatives: new approach to 2H-chromenes?

Organic & Biomolecular Chemistry Pub Date: 2014-10-01 DOI: 10.1039/C4OB01979B

Abstract

2H-Chromene is an important structural motif that exists in natural products and non-natural compounds possessing interesting biological activities. In this investigation, a highly efficient approach toward 2H-chromenes has been developed based on palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrenes. The mechanism of this reaction is proposed that involves the formation of vinyl palladium by carbene migratory insertion and the intramolecular nucleophilic substitution.

Graphical abstract: Palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrene derivatives: new approach to 2H-chromenes
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