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Issue 7, 2018
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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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Submitted
20 Nov 2017
Accepted
11 Jan 2018
First published
15 Jan 2018

Org. Chem. Front., 2018,5, 1096-1100
Article type
Research Article

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, 5, 1096
DOI: 10.1039/C7QO01041A

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