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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 8
BKCSDE 32(8)
August 20, 2011 

 
Title
Practical Synthesis of 1,1-Difluoro- or 1-Fluoroalkenes from 2,2,2-Trifluoroacetophenone Derivatives
Author
Minhyuk Kang, Sun-Ah Lee, Nana Kang, Bongjin Moon *
Keywords
1,1-Difluoroalkenes, 1-Fluoroalkenes, Trifluoroacetophenone, p-Toluene sulfonyl hydrazones
Abstract
Since the discovery of the fact that compounds bearing a vinylic fluoride moiety often exhibit remarkable biological activities such as enzyme inhibitors, many synthetic methods for fluorine-substituted vinylic compounds have been developed. The synthesis of selectively fluorinated building blocks, such as arylsubstituted fluoro-alkenes, also has become an area of interest in recent years. Herein we describe a novel and practical method for the synthesis of 1,1-difluoro- and 1-fluoroalkenes starting from easily accessible trifluoroacetophenone derivatives. Various 1,1-difluoro- and 1-fluoroalkenes were prepared by the reaction of the corresponding tosyl hydrazones that were derived from trifluoroacetophenone derivatives by treating with alkyl or aryllithium reagents via addition-elimination and single electron transfer (SET) mechanism.
Page
3022 - 3030
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