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Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

Hui Qiu, Bin Shuai, Yun-Zhao Wang, Dong Liu, Yue-Gang Chen, Pei‐Sen Gao, Hong‐Xing Ma, Song Chen, Tian‐Sheng Mei

2020Journal of the American Chemical Society217 citationsDOI

Abstract

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.

Topics & Concepts

ChemistryEnantioselective synthesisAtropisomerElectrochemistryCatalysisArylYield (engineering)Reactivity (psychology)Transition metalNickelCombinatorial chemistryOrganic chemistryElectrodeAlkylMetallurgyPhysical chemistryMaterials sciencePathologyMedicineAlternative medicineAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityCatalytic C–H Functionalization Methods
Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers | Litcius