Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1<i>H</i>)-1,2-benziodoxole with B(C₆F₅)₃ Enabling the Electrophilic Cyanation of Silyl Enol Ethers

Abstract

The Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group, 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole (CDBX), with B(C₆F₅)₃, to achieve the catalytic electrophilic cyanation of silyl enol ethers is presented. Mechanistic studies indicate that CDBX is activated through coordination of its cyano group to B(C₆F₅)₃, thus enabling the electrophilic cyanation reaction to occur.