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Direct access to substituted benzo[b]carbazoles through cascade annulation of 2-vinylbenzaldehydes with indoles.

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A highly efficient palladium-catalyzed cascade annulation of 2-vinylbenzaldehydes with indoles has been achieved to afford 6-(3-indolyl)benzo[b]carbazoles under mild conditions in good yield and with excellent regioselectivity. Mechanistic investigations reveal that… Click to show full abstract

A highly efficient palladium-catalyzed cascade annulation of 2-vinylbenzaldehydes with indoles has been achieved to afford 6-(3-indolyl)benzo[b]carbazoles under mild conditions in good yield and with excellent regioselectivity. Mechanistic investigations reveal that the reaction proceeds via double addition of indoles, unexpected intramolecular 1,4-aryl and 1,2-hydrogen migrations, and oxidative aromatization.

Keywords: vinylbenzaldehydes indoles; direct access; benzo carbazoles; annulation vinylbenzaldehydes; cascade annulation

Journal Title: Chemical communications
Year Published: 2019

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