Publications [#234712] of Ross A. Widenhoefer

Journal Articles

  1. Liu, C; Widenhoefer, RA, "Palladium-Catalyzed Cyclization/Carboalkoxylation of Alkenyl Indoles,", J. Am. Chem. Soc., 2004, 126(33), 10246-10247 [15315430], [doi].
    (last updated on 2024/04/24)

    Abstract:
    Reaction of 1-methyl-2-(4-pentenyl)indole with a catalytic amount of PdCl2(CH3CN)2 (5 mol %) and a stoichiometric amount of CuCl2 (3 equiv) in methanol under CO (1 atm) at room temperature for 30 min led to cyclization/carboalkoxylation to form the corresponding tetrahydrocarbazole in 83% isolated yield as a single regioisomer. Palladium-catalyzed cyclization/carboalkoxylation of 2-(4-pentenyl)indoles tolerated substitution along the alkenyl chain and at the internal and cis-terminal olefinic positions. Palladium-catalyzed cyclization/carboalkoxylation tolerated a range of alcohols and was effective for the cyclization of 2-(3-butenyl)indoles, 3-(3-butenyl)indoles, 3-(4-pentenyl)indoles, and 2-(5-hexenyl)indoles.