Asymmetric Fluorination of α‐Aryl Acetic Acid Derivatives with the Catalytic System NiCl 2 –Binap/R 3 SiOTf/2,6‐Lutidine | Zendy

Suzuki Toshiaki | Zendy; Hamashima Yoshitaka | Zendy; Sodeoka Mikiko | Zendy

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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.

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