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Palladium‐Catalyzed Direct Approach to α‐Trifluoromethyl Alcohols by Selective Hydroxylfluorination of gem ‐Difluoroalkenes
Author(s) -
Zhang Bin,
Zhang Xiaofei,
Hao Jian,
Yang Chunhao
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800468
Subject(s) - chemistry , trifluoromethyl , palladium , catalysis , fluorine , combinatorial chemistry , fluoride , organic chemistry , inorganic chemistry , alkyl
A novel palladium‐catalyzed selective hydroxylfluorination of gem ‐difluoroalkenes has been developed. By employing easily obtainable gem ‐difluoroalkenes and NFSI as the fluorine source, the scope, advantages, and limitations of this reaction were investigated. The reaction presents an efficient synthesis to afford a series of α‐trifluoromethyl alcohols in good to excellent yields. Furthermore, this reaction probably proceeds via oxidation of Pd 0 to Pd II fluoride complex by NFSI, followed by fluoropalladation of gem ‐difluoroalkenes to generate an α‐trifluoromethylbenzyl–Pd intermediate. And this strategy offers more possibilities for the construction of other bonds, such as C–C, C–N and C–S.