Chemoselective acyl C–O bond activation in esters for Suzuki–Miyaura coupling

Abstract

Exploitation of the low binding affinity of NHC–palladium complex for the carbonyl oxygen of ester to form three-centered transition state led to the discovery of Suzuki–Miyaura coupling via unprecedented C(acyl)–O bond cleavage. The use of bulky NHC ligand resulted in direct coupling as it prevented decarbonylation of ester. This access to alternative chemoselectivity by careful selection has extended the synthetic portfolio of esters for the diversification of interesting molecular scaffolds.