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Nickel/Photoredox‐Catalyzed Asymmetric Reductive Cross‐Coupling of Racemic α‐Chloro Esters with Aryl Iodides
Author(s) -
Guan Haixing,
Zhang Qianwen,
Walsh Patrick J.,
Mao Jianyou
Publication year - 2020
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.201914175
Subject(s) - aryl , catalysis , chemistry , electrophile , nickel , coupling reaction , combinatorial chemistry , reductive elimination , nonsteroidal , organic chemistry , coupling (piping) , materials science , alkyl , medicine , metallurgy , pharmacology
Abstract A unique nickel/organic photoredox co‐catalyzed asymmetric reductive cross‐coupling between α‐chloro esters and aryl iodides is developed. This cross‐electrophile coupling reaction employs an organic reductant (Hantzsch ester), whereas most reductive cross‐coupling reactions use stoichiometric metals. A diverse array of valuable α‐aryl esters is formed under these conditions with high enantioselectivities (up to 94 %) and good yields (up to 88 %). α‐Aryl esters represent an important family of nonsteroidal anti‐inflammatory drugs. This novel synergistic strategy expands the scope of Ni‐catalyzed reductive asymmetric cross‐coupling reactions.