A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols
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2020
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The Royal Society of Chemistry
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Martín-Mejías I, Aragoncillo C, Yanai H, Hoshikawa S, Fujimoto Y, Matsumoto T, Almendros, P. A Catalyst-Free Bis(triflyl)ethylation/Benzannulation Reaction: Rapid Access to Carbazole-Based Superacidic Carbon Acids from Alkynols. Chem Commun 2020, 56, 1795-1798.
Abstract
Carbazoles possessing Tf2CHCH2 groups were obtained by the reaction of 1-(indol-2-yl)but-3-yn-1-ols with in situ-generated Tf2CQCH2 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