Carbazoles from the [4C+2C] Reaction of 2,3-Allenols with Indoles.

Chemistry

Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, 310027, Zhejiang, P.R. China.

Published: December 2016

A mild and efficient method using readily available 1-aryl-2,3-allenols and unprotected-N indoles, Au -catalyzed cyclization, and aromatization to afford the final [4C+2C] products, carbazoles 4, with an excellent selectivity, is reported. The reaction demonstrates excellent regioselectivity and allows the N-H unit to undergo reactivity unprotected. A mechanism involving a spiropolycyclic intermediate has been proposed and synthetic application is also demonstrated.

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http://dx.doi.org/10.1002/chem.201604317DOI Listing

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