Baylis–Hillman reaction
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In organic chemistry, the Baylis–Hillman, Morita–Baylis–Hillman, or MBH reaction is a carbon-carbon bond-forming reaction between an activated alkene and a carbon electrophile in the presence of a nucleophilic catalyst, such as a tertiary amine or phosphine. The product is densely functionalized, joining the alkene at the α-position to a reduced form of the electrophile (e.g. in the case of an aldehyde, an allylic alcohol).[1][2]
![Baylis-Hillman reaction](http://upload.wikimedia.org/wikipedia/commons/thumb/7/7f/MBH_general_scheme.png/640px-MBH_general_scheme.png)
(Morita–)Baylis–Hillman reaction | |
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Named after | Ken-ichi Morita Anthony B. Baylis Melville E. D. Hillman |
Reaction type | Coupling reaction |
Identifiers | |
Organic Chemistry Portal | baylis-hillman-reaction |
RSC ontology ID | RXNO:0000076 |
The reaction is named for Anthony B. Baylis and Melville E. D. Hillman, two of the chemists who developed the reaction at Celanese; and K. Morita, who published earlier work[3] on the same.
The MBH reaction offers several advantages in organic synthesis:
- It combines easily prepared starting materials with high atom economy.
- It requires only mild conditions and does not require any transition metals.
- Asymmetric synthesis is possible from prochiral electrophiles.
- The product's dense functionalization enables many further transformations.
Its disadvantage is that the reaction is extremely slow.