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Hegedus indole synthesis

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TheHegedus indole synthesis is aname reaction inorganic chemistry that allows for the generation ofindoles throughpalladium(II)-mediated oxidative cyclization of ortho-alkenyl anilines.^[1]^[2]^[3]^[4]^[5]^[6] The reaction can still take place fortosyl-protected amines.^[4]

2-Allylaniline can be converted to2-Methylindole using the Hegedus indole synthesis.^[1]

^^a ^bHegedus, Louis S.; Allen, Gary F.; Waterman, Edward L. (1976-04-01). "Palladium assisted intramolecular amination of olefins. A new synthesis of indoles".Journal of the American Chemical Society.98 (9):2674–2676.doi:10.1021/ja00425a051.
^Hegedus, Louis S.; Allen, Gary F.; Bozell, Joseph J.; Waterman, Edward L. (1978-08-01). "Palladium-assisted intramolecular amination of olefins. Synthesis of nitrogen heterocycles".Journal of the American Chemical Society.100 (18):5800–5807.doi:10.1021/ja00486a035.
^Hegedus, Louis S.; Winton, Peter M.; Varaprath, Sudarsanan (1981-05-01). "Palladium-assisted N-alkylation of indoles: attempted application to polycyclization".The Journal of Organic Chemistry.46 (11):2215–2221.doi:10.1021/jo00324a004.
^^a ^bHarrington, Peter J.; Hegedus, Louis S. (1984-07-01). "Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approaches to ergot alkaloids".The Journal of Organic Chemistry.49 (15):2657–2662.doi:10.1021/jo00189a001.
^Wang, Zerong (15 September 2010).Comprehensive Organic Name Reactions and Reagents.doi:10.1002/9780470638859.conrr302.ISBN 9780470638859.
^Li, Jie Jack (2006).Name Reactions A Collection of Detailed Reaction Mechanisms. Springer. p. 289.ISBN 978-3-540-30030-4.