Facile Approach to Diverse Diarylmethane Scaffolds via DBU-Catalyzed 1,6-Addition Reaction: Discovery of an Antibacterial Agent.

Herein, a DBU-catalyzed 1,6-Michael addition of para-quinone methides (p-QMs) under mild reaction conditions with high efficiency (turnover number up to 103) and good to excellent yields is reported. The transformation proceeds smoothly with a range of nucleophiles, providing diverse diarylmethane scaffolds with good efficiency. Mechanistic studies revealed that DBU is an excellent proton acceptor and donor and that DBU can promote the addition of methanol to p-QMs. A preliminary investigation was also conducted of the antibacterial properties of the products.