Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy

A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation.