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Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles
- Authors
- Tambe, Shrikant D.; Iqbal, Naeem; Cho, Eun Jin
- Issue Date
- Nov-2020
- Publisher
- American Chemical Society
- Citation
- Organic Letters, v.22, no.21, pp 8550 - 8554
- Pages
- 5
- Journal Title
- Organic Letters
- Volume
- 22
- Number
- 21
- Start Page
- 8550
- End Page
- 8554
- ISSN
- 1523-7060
1523-7052
- Abstract
- A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C-N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C-N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles. © 2020 American Chemical Society. All rights reserved.
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