Azo Coupling of Indoles Revisited: Synthesis of Biindolyl Photoswitches via the Azo-Coupling/C-H Functionalization Domino Approach.

Autor: Bondarev VL; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Festa AA; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Storozhenko OA; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Golantsov NE; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Pappula V; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Tskhovrebov AG; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Varlamov AV; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia., Voskressensky LG; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, 117198 Moscow, Russia.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Sep 15; Vol. 88 (18), pp. 12949-12957. Date of Electronic Publication: 2023 Aug 25.
DOI: 10.1021/acs.joc.3c00794
Abstrakt: When azo coupling of aryldiazonium salts with indoles was carried out in aprotic nonpolar solvent on air, a pseudo-three-component reaction has been discovered. Azo coupling is followed by a nucleophilic addition of a second indole unit to the indolium intermediate; aromatization and oxidation are achieved under air.
Databáze: MEDLINE