Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles | Zendy

Houng Kang | Zendy; Young Eun Lee | Zendy; Peddiahgari Vasu Govardhana Reddy | Zendy; Sangeeta Dey | Zendy; Scott E. Allen | Zendy; Kyle A. Niederer | Zendy; Paul D. Sung | Zendy; Kirsten A. Hewitt | Zendy; Carilyn Torruellas | Zendy; Madison R. Herling | Zendy; Marisa C. Kozlowski | Zendy

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Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

Author(s) -

Houng Kang,

Young Eun Lee,

Peddiahgari Vasu Govardhana Reddy,

Sangeeta Dey,

Scott E. Allen,

Kyle A. Niederer,

Paul D. Sung,

Kirsten A. Hewitt,

Carilyn Torruellas,

Madison R. Herling,

Marisa C. Kozlowski

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02552

Subject(s) - chemistry , oxidizing agent , vanadium , phenols , lewis acids and bases , oxidative coupling of methane , catalysis , ligand (biochemistry) , coupling (piping) , oxidative phosphorylation , organic chemistry , combinatorial chemistry , receptor , mechanical engineering , biochemistry , engineering

The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Brønsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee.

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