Regioselective C 3 Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles

Herein, we describe an efficient transition-metal-free regioselective C alkylation of indoles for the synthesis of bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as the oxidant to oxidize the alcohols in the presence of a strong base and the reaction avoids the use of transition...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-02, Vol.89 (3), p.1846-1857
Main Authors: Zhang, Ruiqin, Ma, Renchao, Chen, Rener, Wang, Lei, Ma, Yongmin
Format: Article
Language:English
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Summary:Herein, we describe an efficient transition-metal-free regioselective C alkylation of indoles for the synthesis of bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as the oxidant to oxidize the alcohols in the presence of a strong base and the reaction avoids the use of transition metals such as Ru and Mn. The protocol provides a favorable route to access biologically active compounds such as arundine, vibrindole A, and turbomycin B.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02551