ortho‐Selective Suzuki Coupling of Dichlorophenol and Dichlorobenzylalcohol in Water under Palladium Catalysis Directed by Noncovalent Interactions and Computational Analysis

Abstract

The use of attractive noncovalent interactions is emerging as a versatile approach to address site‐selectivity challenges. Herein, we report ortho‐selective Suzuki coupling reactions in water of 2,3‐dichloroarenes and 2,4‐dichloroarenes bearing a hydroxy group in the presence of a palladacycle catalyst and directed by noncovalent interactions. Various ortho‐substituted arylphenols and arylbenzyl alcohols were obtained in good to excellent yields with high selectivity. Density functional theory (DFT) calculations and ab initio molecular dynamics (AIMD) simulations suggested that the ortho‐selective Suzuki coupling of dichlorophenols and dichlorobenzyl alcohols occurred through electrostatic interactions and hydrogen bonding interactions, respectively.