4.8 Article

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 45, Pages 19112-19120

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c08562

Keywords

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Funding

  1. NSFC [21925109, 21772170, 21702182, 21873081]
  2. Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support [ZJWR0108]
  3. Fundamental Research Funds for the Central Universities [2020XZZX00202]
  4. State Key Laboratory of Clean Energy Utilization [ZJUCEU2020007]

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The study reports a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by tailor-made amino acid ligands. A novel noncovalent interaction was found critical for the chiral induction, resulting in high yields and excellent enantioselectivities of C2-alkylated indoles. DFT calculations revealed the reaction mechanism and origins of chiral induction in the stereodetermining alkene insertion step.
Enantioselective hydroarylation of unactivated terminal akenes constitutes a prominent challenge in organic chemistry. Herein, we reported a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in the C-H activation area, arising from the molecular recognition among the organocobalt(III) intermediate, the coordinated alkene, and the well-designed chiral ligand. A broad range of C2-alkylated indoles were obtained in high yields and excellent enantioselectivities. DFT calculations revealed the reaction mechanism and elucidated the origins of chiral induction in the stereodetermining alkene insertion step.

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