Baylis-Hillman reaction

Also known as: Morita-Baylis-Hillman reaction

Schematic of the Baylis-Hillman reaction. Reagents: α-β unsaturated carbonyl compound, aldehyde, activated ketone, carbon electrophiles, DABCO, Et3N, PR3.

The Baylis-Hillman reaction is an organic reaction used to form a C-C bond between an α-β unsaturated carbonyl compound and an aldehyde, activated ketone, or other carbon electrophiles. This reaction is most commonly catalyzed by DABCO but other tertiary amines or phosphines can also be used as catalysts. The catalyst activates the conjugated carbonyl compound to form a stabilized nucleophilic anion which subsequently attacks the electrophile. The reaction proceeds to afford the final product and regenerate the catalyst.[1]


Mechanism of the Baylis-Hillman reaction. Baylis–Hillman Reaction Catalytic Cycle.


Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972