A facile one-pot benzylation of sodium enolates using trifluoromethanesulfonic anhydride and diphenyl sulfoxide.
A facile one-pot C-benzylation of various sodium enolates derived from methyl malonate, beta-ketoesters, a beta-cyanoester, a beta-cyanosulfone, ketones and a carboxylic ester is reported. Reaction of alkoxydiphenylsulfonium salts formed by treating various benzyl alcohols with diphenyl sulfide bis(trifluoromethanesulfonate) (derived from trifluoromethanesulfonic anhydride and diphenyl sulfoxide) proceeded smoothly, and the corresponding C-benzylated products were afforded in good to high yields.
Takuwa
Tomofumi
T
Center for Basic Research, The Kitasato Institute, 6-15-5 (TCI) Toshima, Tokyo 114-0003, Japan.
Minowa
Tomofumi
T
Fujisawa
Hidehiko
H
Mukaiyama
Teruaki
T
D001554:Benzene / Q000138:chemical synthesis*; D001555:Benzene Derivatives / Q000138:chemical synthesis*; D008698:Mesylates / Q000138:chemical synthesis*; D017670:Sodium Compounds / Q000138:chemical synthesis*; D013678:Technology, Pharmaceutical / Q000379:methods*
D001555:Benzene Derivatives; D008698:Mesylates; D017670:Sodium Compounds; C048860:diphenyl sulfoxide; D001554:Benzene; C012077:trifluoromethanesulfonic acid