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Nucleophilic Difluoro(phenylsulfonimidoyl)methylation of Unactivated Alkyl Bromides with PhSO(NTBS)CF 2 H: Facile Entry into gem ‐Difluoroalkenes
Author(s) -
Shen Xiao,
Liu Qinghe,
Ni Chuanfa,
Hu Jinbo
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400403
Subject(s) - chemistry , alkyl , nucleophile , methylation , nucleophilic substitution , medicinal chemistry , base (topology) , nucleophilic addition , combinatorial chemistry , organic chemistry , catalysis , biochemistry , gene , mathematical analysis , mathematics
Abstract An efficient nucleophilic difluoro(phenylsulfonimidoyl)methylation of unactivated primary alkyl bromides with PhSO(NTBS)CF 2 H has been developed. It is particularly remarkable that, when 1.5 equiv. of alkyl bromides are used, the substitution products are obtained in moderate to excellent yields. The prepared difluoro(phenylsulfonimidoyl)methylated alkanes can be readily transformed to gem ‐difluoroalkenes via base‐mediated β ‐elimination reaction.