Bu4NI/tBuOOH catalyzed, α-regioselective cross-dehydrogenative coupling of BODIPY with allylic alkenes and ethers

Abstract

A Bu₄NI/tBuOOH-catalyzed, highly regioselective cross-dehydrogenative coupling (CDC) of the α-C–H bond(s) of the BODIPY core has been developed. The α-regioselective alkylation reaction utilizes easily accessible coupling partners, namely commercial allylic alkenes and ethers – even common, inert organic solvents, such as tetrahydrofuran, diethyl ether and 1,4-dioxane. The high α-regioselectivity of this CDC reaction is attributable to the radical process involved and provides a facile access to a variety of α-functionalized BODIPYs, which are hard to access through current synthetic methods.