Palladium-catalyzed alkynylative [5+1] carboannulation of 1,3-diarylprop-2-yn-1-yl acetates with terminal alkynes enabled by C-H functionalization

A new method for the synthesis of 3-ethynyl-1-methylene-1,2-dihydronaphthalenes via copper-promoted palladium-catalyzed intermolecular alkynylative [5 + 1] carboannulation of 1-arylphenyl-prop-2-yn-1-yl acetates involving C-H functionalization is described. Two terminal alkyne molecules serve as an alkynylation reagent and a one-carbon unit to enable alkynylative [5 + 1] carboannulation with excellent selectivity control, broad substrate scope and good tolerance of functional groups.

Automated summary

A new method for the synthesis of 3-ethynyl-1-methylene-1,2-dihydronaphthalenes is described, involving copper-promoted palladium-catalyzed intermolecular alkynylative [5 + 1] carboannulation of 1-arylphenyl-prop-2-yn-1-yl acetates. The method shows excellent selectivity control, broad substrate scope, and good tolerance of functional groups by using two terminal alkyne molecules as alkynylation reagent and a one-carbon unit.