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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

Toshimichi Ohmura*, Kaito Yagi, Takeru Torigoe, Michinori Suginome*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email: ohmurasbchem.kyoto-u.ac.jp, suginomesbchem.kyoto-u.ac.jp

T. Ohmura, K. Yagi, T. Torigoe, M. Suginome, Synthesis, 2021, 53, 3057-3064.

DOI: 10.1055/a-1511-1025 (free Supporting Information)


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Abstract

IrCl(DTBM-SEGPHOS)(C2H4) catalyzes an efficient intramolecular addition of a C(sp3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl-N,N-dimethylanilines in mesitylene at 150C. The intramolecular C(sp3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in very good yields.

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Key Words

C-H bond activation, addition reaction, cyclization, iridium, indoles


ID: J66-Y2021