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Synthesis 2021; 53(17): 3057-3064
DOI: 10.1055/a-1511-1025
DOI: 10.1055/a-1511-1025
special topic
Bond Activation – in Honor of Prof. Shinji Murai
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
This work was partially supported by Japan Society for the Promotion of Science (JSPS KAKENHI Grant Numbers JP20H05674 and JP21H01937), by Asahi Glass Foundation, and by Tonen General Sekiyu Research/Development Encouragement and Scholarship Foundation.
Abstract
Intramolecular addition of a C(sp3)–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 °C. The intramolecular C(sp3)–H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1511-1025.
- Supporting Information
Publikationsverlauf
Eingereicht: 29. April 2021
Angenommen nach Revision: 18. Mai 2021
Accepted Manuscript online:
18. Mai 2021
Artikel online veröffentlicht:
15. Juni 2021
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For recent reviews, see:
Intramolecular addition of a C(sp3)–H bond α to nitrogen across C–C double bonds to form carbocycles has also been reported:
For examples of IrCl(L)2(C2H4), see: