45990-93-0Relevant academic research and scientific papers
Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines
Ohmura, Toshimichi,Yagi, Kaito,Torigoe, Takeru,Suginome, Michinori
supporting information, p. 3057 - 3064 (2021/06/28)
Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.
Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)?H Addition to Carbon–Carbon Double Bonds
Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
supporting information, p. 14272 - 14276 (2017/10/23)
Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)?H bond across a carbon–carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C?H bond, followed by intramolecular carboiridation and subsequent reductive elimination.
