102012-60-2Relevant articles and documents
Anhydrous Hydrogen Iodide-Mediated Reductive Indolization of in Situ-Generated Cyclopropyl Hydrazones
Yasui, Motohiro,Fujioka, Hiroki,Takeda, Norihiko,Ueda, Masafumi
supporting information, p. 43 - 47 (2021/12/17)
Fischer-type indolization of N-aryl-C-cyclopropyl hydrazones generated in situ followed by chemoselective reduction using tert-butyl iodide as an anhydrous HI generator was developed. This protocol provides indoles bearing carboxylic acid derivative units. A series of control experiments indicated the HI-mediated formation and reduction of spirocyclopropyl indolenines. Anhydrous HI functions as a Br?nsted acid as well as a reducing agent, facilitating the successful conversion of unstable reaction intermediates and iodinated mixtures in equilibrium.