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Decarboxylative Perfluoroalkylation of Vinyl Bromides with Copper(I) Perfluorocarboxylato Complexes
Author(s) -
Wu Chuyi,
Huang Yangjie,
Zhang Zhongxing,
Weng Zhiqiang
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600348
Subject(s) - trifluoromethylation , chemistry , trifluoromethyl , nitrile , reagent , copper , medicinal chemistry , organic chemistry , nitro , polymer chemistry , alkyl
A new decarboxylative perfluoroalkylation of vinyl bromides has been developed. The use of copper(I) trifluoroacetate complex (phen)Cu(O 2 CCF 3 ) ( 1 ) and perfluorocarboxylate complexes [(phen) 2 Cu](O 2 CR F ) ( 2 ; R F =C 2 F 5 , n ‐C 3 F 7 , n ‐C 4 F 9 , n ‐C 5 F 11 ) as reagents allows for the efficient synthesis of trifluoromethylated and perfluoroalkylated olefins, respectively. Vinyl bromides comprising a range of functionalities (e.g., methoxy, ester, nitrile, nitro, trifluoromethyl, chloride, and benzo[ d ][1,3]dioxole) were successfully accommodated. The decarboxylative trifluoromethylation and perfluoroalkylation reactions also proceeded with retention of the double‐bond stereochemistry of alkenes after the reaction was completed.