Journal
TETRAHEDRON LETTERS
Volume 51, Issue 47, Pages 6150-6152Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.09.068
Keywords
Fluorine; (Phenylsulfonyl)difluoromethylation; Difluoroalkene; Trifluoromethylation; Nucleophilic substitution; Fluoroalkylation
Categories
Funding
- National Natural Science Foundation of China [20502029, 20772144, 20825209, 20832008]
- Chinese Academy of Sciences
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Nucleophilic (phenylsulfonyl)difluoromethylation of both alkyl iodides and bromides was successfully accomplished by using CsF/15-crown-5 as an initiating system in DME, and the amount of 15-crown-5 was found to be critical to the yield of the product. The prepared (phenylsulfonyl)difluoromethylated alkanes were converted into gem-difluoroalkenes by a base-mediated 1,2-elimination reaction, and the latter species could be further transformed into trifluoromethyl compounds in the presence of KF/18-crown-6 or TBAF. (C) 2010 Elsevier Ltd. All rights reserved.
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