Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

Chemistry. 2016 Nov 14;22(47):16787-16790. doi: 10.1002/chem.201604504. Epub 2016 Oct 11.

Abstract

A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.

Keywords: C−H borylation; C−O bond activation; decarbonylative cross-coupling; esters; nickel.