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Copper‐Catalyzed Difunctionalization of Activated Alkynes by Radical Oxidation–Tandem Cyclization/Dearomatization to Synthesize 3‐Trifluoromethyl Spiro[4.5]trienones
Author(s) -
Hua HuiLiang,
He YuTao,
Qiu YiFeng,
Li YingXiu,
Song Bo,
Gao Pin,
Song XianRong,
Guo DongHui,
Liu XueYuan,
Liang YongMin
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405672
Subject(s) - trifluoromethylation , trifluoromethyl , chemistry , reagent , tandem , catalysis , copper , combinatorial chemistry , double bond , organic chemistry , medicinal chemistry , alkyl , materials science , composite material
A copper‐catalyzed difunctionalizing trifluoromethylation of activated alkynes with the cheap reagent sodium trifluoromethanesulfinate (NaSO 2 CF 3 or Langlois’ reagent) has been developed incorporating a tandem cyclization/dearomatization process. This strategy affords a straightforward route to synthesis of 3‐(trifluoromethyl)‐spiro[4.5]trienones, and presents an example of difunctionalization of alkynes for simultaneous formation of two carbon–carbon single bonds and one carbon–oxygen double bond.