Enhanced basicity of an electron donor-acceptor complex

An electron donor - acceptor (EDA) complex forms between 1,4-dicyanobenzene and N -phenylpyrrolidine, which are coupling partners for the α-aminoarylation photoredox reaction. Calculations and experiments demonstrate the EDA complex is a better base than N -phenylpyrroline. A re-analysis of the α-aminoarylation reaction suggests that the EDA complex is a proton acceptor in the reaction. Formation of an electron donor-acceptor (EDA) complex increases the basicity of an amine, allowing the EDA complex to function as a primary proton acceptor in a photoredox reaction.