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Pd II ‐Catalyzed Regio‐ and Enantioselective Oxidative C−H/C−H Cross‐Coupling Reaction between Ferrocenes and Azoles
Author(s) -
Cai ZhongJian,
Liu ChenXu,
Gu Qing,
Zheng Chao,
You ShuLi
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813887
Subject(s) - regioselectivity , chemistry , enantioselective synthesis , catalysis , combinatorial chemistry , palladium , bond cleavage , stereochemistry , reactivity (psychology) , coupling reaction , oxidative addition , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
Asymmetric C−H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C−H/C−H cross‐coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C−H bond cleavage of azoles is likely proceeding through a S E Ar process and may not be a turnover limiting step.