- Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3
-
We report the FeCl3-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air). No functional group is required on the arene nucleophile: one of its C-H bonds is added to the C2=C3 double bond of the indole nucleus in a Friedel-Crafts-type reaction. This dearomatisation process delivered a broad range of C2-arylated indolines.
- Nandi, Raj Kumar,Ratsch, Friederike,Beaud, Rodolphe,Guillot, Régis,Kouklovsky, Cyrille,Vincent, Guillaume
-
p. 5328 - 5331
(2016/04/26)
-
- Intramolecular cooperative C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines to give o-(N-Acylamino)aryl ketones and multisubstituted indoles
-
A copper-catalyzed C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2-aminophenyl)-bis-(1,3-dicarbonyl) copper species was clearly observed by a time-course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3-dicarbonyl compound were coupled with 2-iodoaniline by C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.
- Xing, Qi,Lv, Hui,Xia, Chungu,Li, Fuwei
-
supporting information
p. 8591 - 8596
(2015/06/02)
-