Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature

Angew Chem Int Ed Engl. 2014 Feb 10;53(7):1799-803. doi: 10.1002/anie.201308855. Epub 2014 Jan 13.


A new catalytic system based on a Zn(II) NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for CX borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes.

Keywords: N-heterocyclic carbenes; Suzuki-Miyaura; boronate esters; cross-coupling; homogeneous catalysis.