Hegedus indole synthesis
Named after Louis S. Hegedus
Reaction type Ring forming reaction

The Hegedus indole synthesis is a name reaction in organic chemistry that allows for the generation of indoles through palladium(II)-mediated oxidative cyclization of ortho-alkenyl anilines.[1][2][3][4][5][6] The reaction can still take place for tosyl-protected amines.[4]

Application

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

References

  1. 1 2 Hegedus, 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.
  2. ↑ 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.
  3. ↑ 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.
  4. 1 2 Harrington, 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.
  5. ↑ Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr302. ISBN 9780470638859.
  6. ↑ Li, Jie Jack (2006). Name Reactions A Collection of Detailed Reaction Mechanisms. Springer. p. 289. ISBN 978-3-540-30030-4.


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