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Oxygen‐Linked Cyclopentadienyl Rhodium(III) Complexes‐Catalyzed Asymmetric C−H Arylation of Benzo[ h ]quinolines with 1‐Diazonaphthoquinones
Author(s) -
Pan Chongqing,
Yin SiYong,
Wang ShaoBo,
Gu Qing,
You ShuLi
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202103638
Subject(s) - cyclopentadienyl complex , rhodium , chemistry , electrophile , catalysis , yield (engineering) , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy
Abstract Chiral cyclopentadienyl rhodium (CpRh) complex‐catalyzed asymmetric C−H functionalization reactions have witnessed a significant progress in organic synthesis. In sharp contrast, the reported chiral Cp ligands are limited to C‐linked Cp and are often synthetically challenging. To address these issues, we have developed a novel class of tunable chiral cyclopentadienyl ligands bearing oxygen linkers, which were efficient catalysts for C−H arylation of benzo[ h ]quinolines with 1‐diazonaphthoquinones, affording axially chiral heterobiaryls in excellent yields and enantioselectivity (up to 99 % yield, 98.5:1.5 er). Mechanistic studies suggest that the reaction is likely to proceed by electrophilic C−H activation, and followed by coupling of the cyclometalated rhodium(III) complex with 1‐diazonaphthoquinones.