A catalyst-free bis(triflyl)ethylation/benzannulation reaction: Rapid access to carbazole-based superacidic carbon acids from alkynols

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Abstract

Carbazoles possessing Tf2CHCH2 groups were obtained by the reaction of 1-(indol-2-yl)but-3-yn-1-ols with in situ-generated Tf2CCH2 through vicinal difunctionalisation of the alkyne moiety, where the vinyl-type carbocation intermediate was selectively attacked by the indole moiety and not by the carbanion moiety.

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Martín-Mejías, I., Aragoncillo, C., Yanai, H., Hoshikawa, S., Fujimoto, Y., Matsumoto, T., & Almendros, P. (2020). A catalyst-free bis(triflyl)ethylation/benzannulation reaction: Rapid access to carbazole-based superacidic carbon acids from alkynols. Chemical Communications, 56(12), 1795–1798. https://doi.org/10.1039/c9cc08930f

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