Bayliss-Hillman Reaction – Online Organic Chemistry Tutor

Bayliss-Hillman Reaction - Online Organic Chemistry Tutor

The Bayliss–Hillmann reaction is a coupling organic chemical reaction that leads to the formation of a C-C bond between an aldehyde or an active ketone and an electrophile such as α,β carbonyl compounds. The reaction occurs in the presence of a tertiary amine and phosphine and is mostly DABCO (1,4 diazebicyclo). [2.2.2] Octane tertiary amine is used.

Reaction Discovery Anthony B. Bayliss and Melville ED Hillman in 1972. The reaction is also known as the Morita–Bellis–Hillmann reaction or the MBH reaction.

mechanism of reaction– First the carbonyl compound is activated by a catalyst to form a nucleophilic anion, which further attacks the electrophile. The reaction is proceeded to form the desired product. The catalyst is regenerated in a reaction that goes through a cycle of re-catalysis.

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