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Versatile synthesis of polyfunctionalized carbazoles from (3-iodoindol-2-yl)butynols via a gold-catalyzed intramolecular iodine-transfer reaction

AuthorsAlcaide, Benito ; Almendros, Pedro ; Alonso, J. M.; Busto, Eduardo; Fernández, I.; Ruiz, M. P.; Xiaokaiti, G.
KeywordsDensity functional calculations
Issue Date2015
PublisherAmerican Chemical Society
CitationACS Catalysis 5: 3417-3421 (2015)
AbstractThe controlled gold-catalyzed preparation of 3-iodo 2,4,6-trisubstituted 9H-carbazoles has been developed by starting from (3-iodoindol-2-yl)butynols. These results could be explained through an initial 6-endo-dig alkyne carbocyclization by chemo- and regiospecific attack of the C3-indole position at the external alkyne carbon followed by a stepwise 1,3-iodine transfer and dehydration. This reaction outcome for the gold-catalyzed transformation of (3-iodoindol-2-yl)alkynols sharply contrasts with that observed for conventional metal-catalyzed processes of iodoarenes, because iodine transfer is feasible. This selective reaction has been studied experimentally; additionally, its mechanism has been investigated by means of density functional theory calculations.
Identifiersdoi: 10.1021/acscatal.5b00471
issn: 2155-5435
Appears in Collections:(IQOG) Artículos
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