The formation of a C-C single bond between the α-position of a conjugated carbonyl compound and a carbon electrophile in the presence of a nucleophilic Lewis Base catalyst is known as the Baylis-Hillman reaction. A Michael addition of the catalyst occurs at the β-position of the conjugated carbonyl compound, forming a zwitterionic enolate. The enolate attacks the carbonyl compound, yielding another zwitterion, which undergoes an elimination to release the catalyst. A final protonation affords the desired product.
- Reagents: Nucleophilic Lewis Base Catalyst (3° Amine (DABCO, quinuclidine, etc.))
- Reactant: Conjugated Carbonyl Compound (e.g. Ester, Amide) and Carbon Electrophile (Aldehyde or Activated Ketone)
- Product: Coupled product
Mechanism
Top Citations
Original Paper
- Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972
Related Reactions
- Morita-Baylis-Hillman reaction
