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Pyrroloindolone Synthesis via a Cp*CoIII-Catalyzed Redox-Neutral Directed C–H Alkenylation/Annulation Sequence
Abstract
A unique synthetic utility of a Cp*Co(III) catalyst in comparison with related Cp*Rh(III) catalysts is described. A C2-selective indole alkenylation/annulation sequence proceeded smoothly with catalytic amount of a [Cp*Co(III)(C6H6)](PF6)2 complex and KOAc. Intramolecular addition of an alkenyl-Cp*Co species to a carbamoyl moiety gave pyrroloindolones in 58-89% yield in one pot. Clear difference was observed between the catalytic activity of the Cp*Co(III) complex and those of Cp*Rh(III) complexes, highlighting the unique nucleophilic activity of the organocobalt species. The Cp*Co(III) catalysis was also suitable for simple alkenylation process of N-carbamoyl indoles, and broad range of alkynes, including terminal alkynes, were applicable to give C2-alkenylated indoles in 50-99% yield. Mechanistic studies on C-H activation step under Cp*Co(III) catalysis with the aid of an acetate unit as well as evaluation of the difference between organo-Co(III) species and organo-Rh(III) species are also described.
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Metadata
- Authors
- Ikemoto, H., Yoshino, T., Sakata, K., Matsunaga, S., & Kanai, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-03-31
- Volume
- 136
- Issue
- 14
- Pages
- 5424-5431
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2331468909
- Cited by
- 466
- References
- 19
- FWCI
- 34.83
- Type
- journal article
- Language
- en
- Open access
- closed
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