A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform.
A simple strategy avoiding the decomposition of a naked trifluoromethyl anion to difluorocarbene by a sterically very demanding organo-superbase without the help of a trifluoromethyl anion reservoir such as DMF is reported. The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 base afforded trifluoromethyl alcohols in high yields.
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Showa-ku, Nagoya, Japan.
Hiroyuki
H
Kawai
Zhe
Z
Yuan
Etsuko
E
Tokunaga
Norio
N
Shibata
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D005617:Chlorofluorocarbons, Methane; D006845:Hydrocarbons, Fluorinated; C121084:difluorocarbene; C009554:fluoroform