Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Z...

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Published inJournal of the American Chemical Society Vol. 142; no. 22; pp. 9872 - 9878
Main Authors Qiu, Hui, Shuai, Bin, Wang, Yun-Zhao, Liu, Dong, Chen, Yue-Gang, Gao, Pei-Sen, Ma, Hong-Xing, Chen, Song, Mei, Tian-Sheng
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 03.06.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORGANONICKEL COMPLEXES
HALIDES
CROSS-COUPLING REACTIONS
ASYMMETRIC SUZUKI-MIYAURA
ACTIVATION
TRANSITION-METAL-COMPLEXES
NICKEL CATALYSIS
AXIALLY CHIRAL COMPOUNDS
C-C
ARYL
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Summary:A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b13117