Abstract
Apart from the use of (trifluoromethyl)trimethylsilane, the scope
of which has been broadened to the synthesis of trifluoromethyl
sulfides, especially those that are bio-active, new and mild processes
for the nucleophilic trifluoromethylation of non-enolizable carbonyl
compounds or disulfides have been discovered from fluoroform or
hemiaminals of trifluoroacetaldehyde and their derivatives. Very
stable hemiaminals of fluoral (as well as their silyl ethers), readily
prepared from commercially available hemiketals, have been designed
as new trifluoromethylating agents. Besides their trifluoromethylating
ability, they can be transformed into silyl or methyl ethers, which
behave, as efficient generators of α-(trifluoromethyl)iminiums
salts and equivalents of difluoromethylcarboxyl anions, respectively.
1 Introduction
2 Sulfur Trifluoromethylation with CF3SiMe3
3 Trifluoromethylation with Fluoroform
4 Trifluoromethylation with Stable Hemiaminals of Fluoral
5 Generation and Uses of Fluoral Iminiums
6 Generation and Uses of Difluorocarboxylate Anions
7 Conclusion
Key words
nucleophilic trifluoromethylation - trifluoromethyl
anion - fluoroform - fluoral hemiaminals - α,α-difluoromethyl
esters/amides
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