Improved Julia−Kocienski Conditions for the Methylenation of Aldehydes and Ketones

2005/11/23 by Christophe Aïssa · 1 citation
Chemistry · Engineering · #Oxidative Organic Chemistry Reactions #Innovative Microfluidic and Catalytic Techniques Innovation #Chemical Synthesis and Reactions

paper · doi:10.1021/jo051693a

openalex publication_date 2005/11/23 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

Abstract

[reaction: see text] The scope of the methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5-ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at -78 degrees C or Cs2CO3 at 70 degrees C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination reactions.

Citations

• A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles.

Cited by

• Julia olefination [wikipedia]