Regio- and stereo-selective decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes via dual C–H bond functionalization

Abstract

A convenient Cu-promoted three-component decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes is developed to provide chain elongated tri-substituted olefins with good chemo-, regio- and stereo-selectivities, and is applied to the radical-type decarbonylative coupling of sugar analogs. Readily available aliphatic aldehydes are readily decarbonylated into 1˙, 2˙ and 3˙ alkyl radicals for the construction of a C(sp³)–C(sp²) bond via radical addition, followed by HAS-arylation to form the C(sp²)–C(sp²) bond.