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Baylis-Hillman Reaction

March 2, 2013

Baylis-Hillman Reaction is also called Morita-Baylis-Hillman which involves the reaction between an electrophile, usually a carbonyl containing compound such as an aldehyde, ketone or imine and an acitivated alkene in the presence of a catalyst such as amine or phosphine to deliver an α-methylene-β-hydroxy carbonyl or α-methylene-β-amino carbonyl adduct.

This reaction is named after three scientist Japanese chemist Ken-ichi Morita, the British chemist Anthony B. Baylis and the German chemist Melville E. D. Hillman.

Baylis-Hillman Reaction

Mechanism of the reaction

  • Michael addition of the nucleophilic trigger catalyst to the activated alkene.
  • Quenching the Zwitterionic adduct with an electrophile.
  • Proton transfer followed by elimination of the catalyst takes place.

Baylis–Hillman reaction mechanism

The most widely accepted MBH (Morita-Baylis-Hillman) mechanism which involves methyl vinyl ketone, benzaldehyde and 1,4-diazabi-cyclo octane.

Scope and Limitations

This reaction tolerates a wide range of activated alkenes. The reaction of aldehydes at atmospheric pressure with DABCO catalyst

Baylis-Hillman Reaction scope and limitations

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