Published TCIMAIL newest issue No.197
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Julia Olefination Reaction
The Julia olefination reaction and its various sub-forms is a useful synthetic method to convert aldehydes to olefins using arylsulfones. Julia olefination has advantages over other olefination techniques in that it offers mild user-friendly conditions over a wide range of substrates. Perhaps the most well-known Julia-Kocienski olefination method, colloquially known as the Modified Julia, uses heteroaromatic sulfone moieties like 1-methyl-2-(methylsulfonyl)benzimidazole to furnish the transformation. The inclusion of heteroatoms into the aromatic handle modifies the mechanistic pathway resulting in a one-pot procedure and the evolution of SO2 gas driving the reaction to completion.
- Reagents:
- Alkylphenyl sulfones, Julia-Kocienski olefination reagents
- Reactants:
- Aldehydes, Ketones
- Products:
- E- and Z-Olefins
- Scheme:
-
- Original literature:
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- Syntheses a l'aide de sulfones v(+)- methode de synthese generale de doubles liaisons.
- Review literature:
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- The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
