Premium
Cobalt‐Catalyzed Enantioselective Negishi Cross‐Coupling of Racemic α‐Bromo Esters with Arylzincs
Author(s) -
Liu Feipeng,
Zhong Jiangchun,
Zhou Yun,
Gao Zidong,
Walsh Patrick J.,
Wang Xueyang,
Ma Sijie,
Hou Shicong,
Liu Shangzhong,
Wang Minan,
Wang Min,
Bian Qinghua
Publication year - 2018
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.201705463
Subject(s) - negishi coupling , enantioselective synthesis , chemistry , olefin fiber , amide , cobalt , catalysis , ether , acetal , yield (engineering) , halide , organic chemistry , amine gas treating , combinatorial chemistry , materials science , metallurgy
The first cobalt‐catalyzed enantioselective Negishi cross‐coupling reaction, and the first arylation of α‐halo esters with arylzinc halides, are disclosed. Employing a cobalt‐bisoxazoline catalyst, various α‐arylalkanoic esters were synthesized in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield). A diverse range of functional groups, including ether, halide, thioether, silyl, amine, ester, acetal, amide, olefin and heteroaromatics is tolerated by this method. This method was suitable for gram‐scale reactions, enabling the synthesis of ( R )‐xanthorrhizol with high enantiopurity. Radical clock experiments support the intermediacy of radicals.