DFT Analysis into the Calcium(II)-Catalyzed Coupling of Alcohols With Vinylboronic Acids: Cooperativity of Two Different Lewis Acids and Counterion Effects

The mechanism of the calcium-catalyzed coupling alcohols with vinylboronic acids has been analyzed by means density functional theory computations. This study reveals that calcium and boron Lewis associate to form a superelectrophile able promote pericyclic group transfer reaction allyl alcohols. With other alcohols, two act synergistically activate OH functionality trigger SNi pathway. These mechanisms are affected nature counterions, which rationalized electronic steric factors.