Intramolecular Addition of a Dimethylamino C(sp3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl-N-methylanilines

被引:5
作者
Ohmura, Toshimichi [1 ]
Yagi, Kaito [1 ]
Torigoe, Takeru [1 ]
Suginome, Michinori [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 17期
基金
日本学术振兴会;
关键词
C-H bond activation; addition reaction; cyclization; iridium; indoles; H BONDS; O BOND; ACTIVATION; COMPLEXES; HYDROAMINOALKYLATION; EFFICIENT; ALPHA; 3-AROYLINDOLES; CYCLIZATION; IRIDIUM(I);
D O I
10.1055/a-1511-1025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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)(C2H4), in mesitylene at 150 degrees C. The intramolecular C(sp(3))-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.
引用
收藏
页码:3057 / 3064
页数:8
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