Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor

Abstract

A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF₃ - or N₃ -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.

Keywords: alkene functionalization; azidation; copper catalysis; radicals; trifluoromethylation.