Regioselective and Redox-Neutral Cp*IrIII-Catalyzed Allylic C-H Alkynylation

Mondal, Shobhan; Pinkert, Tobias; Daniliuc, Constantin G.; Glorius, Frank

Abstract

Herein, we report a Cp*IrIII-catalyzed highly regioselective and redox-neutral protocol for the construction of 1,4-enynes from unactivated olefins and bromoalkynes via intermolecular allylic C−H alkynylation. The developed mild reaction conditions tolerate a broad range of common functional groups, even enabling selective alkynylation of allylic C−H bonds in the presence of other prominent directing groups. Mechanistic experiments including the isolation of a catalytically active IrIII-allyl species support an intermolecular allylic C−H activation followed by an electrophilic alkynylation.