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Rh(III)-Catalyzed regio- and stereoselective bisindolylation of vinyl acetate: an efficient approach toward (E)-1,2-bis(2-indolyl)ethenes

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Abstract

Vinyl acetate was employed as a cheap and convenient vinyl source in an Rh(III)-catalyzed C2-vinylation of indoles, which provides an efficient pathway toward a series of (E)-1,2-bis(2-indolyl)ethenes. Preliminary mechanism studies suggested that N-(2-pyridyl)-2-vinylindoles 2 and rhodacycle 4 were formed as key intermediates during the reaction process. The highly selective bisindolylation of vinyl acetate might be ascribed to the higher reactivity of vinylindoles 2 compared with vinyl acetate in a C–H olefination of N-(2-pyridyl)indoles.

Graphical abstract: Rh(iii)-Catalyzed regio- and stereoselective bisindolylation of vinyl acetate: an efficient approach toward (E)-1,2-bis(2-indolyl)ethenes

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The article was received on 20 Nov 2017, accepted on 11 Jan 2018 and first published on 15 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01041A
Citation: Org. Chem. Front., 2018, Advance Article
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    Rh(III)-Catalyzed regio- and stereoselective bisindolylation of vinyl acetate: an efficient approach toward (E)-1,2-bis(2-indolyl)ethenes

    W. Qin, W. Li, P. Zhu, X. Mo, H. Zhang and T. Wen, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO01041A

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