The Julia olefination (also known as the Julia–Lythgoe olefination) is the chemical reaction used in organic chemistry of phenyl sulfones (1) with aldehydes (or ketones) to give alkenes (olefins)(3) after alcohol functionalization and reductive elimination using sodium amalgam[1][2] or SmI2.[3] The reaction is named after the French chemist Marc Julia.
Julia Olefination Revised Scheme
The utility of this connective olefination reaction arises from its versatility, its wide functional group tolerance, and the mild reaction conditions under which the reaction proceeds.
All four steps can be carried out in a single reaction vessel, and use of R3X is optional. However, purification of the sulfone intermediate 2 leads to higher yield and purity. Most often R3 is acetyl or benzoyl, with acetic anhydride or benzoyl chloride used in the preparation of 2.
The Juliaolefination (also known as the Julia–Lythgoe olefination) is the chemical reaction used in organic chemistry of phenyl sulfones (1) with aldehydes...
synthesis, the fragments 2 and 3 were first coupled together through Juliaolefination in the presence of KHMDS. The resulting intermediate, abbreviated...
acidic than sulfoxides. In the Ramberg–Bäcklund reaction and the Juliaolefination, sulfones are converted to alkenes by the elimination of sulfur dioxide...
1978, Julia died in Paris at the age of 85. Julia was also father to Marc Julia, the French organic chemist who invented the Juliaolefination. Julia collaborated...
discovered the Julia olefination reaction in 1973. Julia was born in 1922 in Paris as son of the renowned mathematician Gaston Julia. Julia studied physics...
another alternative is the Juliaolefination, which uses the carbanion generated from a phenyl sulfone. The Takai olefination based on an organochromium...
The second elimination reaction takes place with sodium amalgam in Juliaolefination style. Wagaman, Michael W.; Bellmann, Erika; Cucullu, Michèle; Grubbs...
Early work with Basil Lythgoe on the scope and stereochemistry of the Juliaolefination with alpha-metallated sulphone reagents emphasised the value of this...
the Brook rearrangement, the Fleming–Tamao oxidation, and the Peterson olefination. The Si–C bond (1.89 Å) is significantly longer than a typical C–C bond...
et al. generated extended alkane functionality by hydroformylation, olefination, and then hydrogenation. Orthogonal tandem catalysis is a "one-pot reaction...
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