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Highly Selective Activation of Vinyl C–S Bonds Over Aryl C–S Bonds in the Pd‐Catalyzed Coupling of ( E )‐(β‐Trifluoromethyl)vinyldiphenylsulfonium Salts: Preparation of Trifluoromethylated Alkenes and Dienes
Author(s) -
Lin Hao,
Dong Xicheng,
Li Yuxue,
Shen Qilong,
Lu Long
Publication year - 2012
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.201200758
Subject(s) - chemistry , trifluoromethyl , aryl , catalysis , medicinal chemistry , coupling reaction , combinatorial chemistry , organic chemistry , polymer chemistry , alkyl
We describe the Suzuki coupling reaction of ( E )‐(β‐trifluoromethyl)vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl C–S bond is much more favorable (11.7 kcal mol –1 ) than that of the aryl C–S bond.