A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols. Issue 12 (17th January 2020)

• Record Type: Journal Article
• Authors: Martín-Mejías, Irene; Aragoncillo, Cristina; Yanai, Hikaru; Hoshikawa, Shoki; Fujimoto, Yuuki; Matsumoto, Takashi; Almendros, Pedro
• Is Part Of: Chemical communications. Volume 56:Issue 12(2020)
• Page Start: 1795
• Page End: 1798
• Publication Date: 2020-01-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc08930f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A metal- and irradiation-free preparation of Tf2 CHCH2 -decorated carbazoles from 1-(indol-2-yl)but-3-yn-1-ols under mild conditions with a 2-fluoropyridinium salt as the Tf2 CCH2 source has been attained in a straightforward and selective manner. Abstract : Carbazoles possessing Tf2 CHCH2 groups were obtained by the reaction of 1-(indol-2-yl)but-3-yn-1-ols with in situ -generated Tf2 CCH2 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.