Premium
Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Secondary α‐(Trifluoromethyl)benzyl Tosylates
Author(s) -
Brambilla Marta,
Tredwell Matthew
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706631
Subject(s) - trifluoromethyl , palladium , aryl , chemistry , catalysis , combinatorial chemistry , coupling reaction , organic chemistry , medicinal chemistry , alkyl
A palladium‐catalyzed C(sp 3 )−C(sp 2 ) Suzuki–Miyaura cross‐coupling of aryl boronic acids and α‐(trifluoromethyl)benzyl tosylates is reported. A readily available, air‐stable palladium catalyst was employed to access a wide range of functionalized 1,1‐diaryl‐2,2,2‐trifluoroethanes. Enantioenriched α‐(trifluoromethyl)benzyl tosylates were found to undergo cross‐coupling to give the corresponding enantioenriched cross‐coupled products with an overall inversion in configuration. The crucial role of the CF 3 group in promoting this transformation is demonstrated by comparison with non‐fluorinated derivatives.