Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles | Zendy

Lei Liu | Zendy; Patrick J. Carroll | Zendy; Marisa C. Kozlowski | Zendy

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Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

Author(s) -

Lei Liu,

Patrick J. Carroll,

Marisa C. Kozlowski

Publication year - 2015

Publication title -

organic letters

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503521b

Subject(s) - regioselectivity , chemistry , tetramer , vanadium , catalysis , oxidative coupling of methane , oxidative phosphorylation , coupling (piping) , selectivity , oxygen , combinatorial chemistry , dimer , photochemistry , organic chemistry , biochemistry , materials science , enzyme , metallurgy

The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho-ortho' coupling pattern were obtained with high selectivity. Further oxidation led to ortho'-ortho' coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.

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