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Asymmetric Fluorination of α‐Aryl Acetic Acid Derivatives with the Catalytic System NiCl 2 –Binap/R 3 SiOTf/2,6‐Lutidine
Author(s) -
Suzuki Toshiaki,
Hamashima Yoshitaka,
Sodeoka Mikiko
Publication year - 2007
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.200701071
Subject(s) - binap , acetic acid , chemistry , aryl , catalysis , asymmetric hydrogenation , medicinal chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , alkyl
Not binary, but trinary : A binary system consisting of Ni(OTf) 2 –binap complex and 2,6‐lutidine failed to promote the asymmetric fluorination of ester equivalents. However, upon the addition of a substoichiometric amount of Et 3 SiOTf to the NiCl 2 –binap/2,6‐lutidine catalyst, the monofluorinated products were obtained in good yield with high enantioselectivity (see example). NFSI= N ‐fluorobenzenesulfonimide, Tf=trifluoromethanesulfonyl.