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Iron-Catalyzed C−C Bond Formation at α-Position of Aliphatic Amines via C−H Bond Activation through 1,5-Hydrogen Transfer
Abstract
C-C bond formation reactions that take place through organoiron species sometimes exhibit radical-like character. The reaction of N-(2-iodophenylmethyl)dialkylamine with a Grignard or diorganozinc reagent in the presence of a catalytic amount of Fe(acac)(3) gives the product resulting from arylation, alkenylation, or alkylation of the sp(3) C-H bond next to the amine group in good to excellent yield. Mechanistic studies including labeling experiments indicate that the reaction involves radical translocation triggered by the formation of a radical-like species by removal of the iodide group.
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Citations
Cited by
3d Transition Metals for C–H Activation
Gandeepan, P., Müller, T., Zell, D., Cera, G., Warratz, S., & Ackermann, L. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00507 · Cited by 2,332
Katalyse von Radikalreaktionen: Konzepte aus Sicht der Radikalchemie
Studer, A., & Curran, D. P. (2016) · Angewandte Chemie · doi:10.1002/ange.201505090 · Cited by 313
Parasram, M., Chuentragool, P., Sarkar, D., & Gevorgyan, V. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b01628 · Cited by 284
Rousseaux, S., Gorelsky, S. I., Chung, B. K. W., & Fagnou, K. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103081n · Cited by 278
Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)‐Catalyzed C−H Alkylation of Azacycles
Tran, A. T., & Yu, J. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201704755 · Cited by 105
Metadata
- Authors
- Yoshikai, N., Mieczkowski, A., Matsumoto, A., Ilies, L., & Nakamura, E.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-04-02
- Volume
- 132
- Issue
- 16
- Pages
- 5568-5569
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2084773984
- Cited by
- 180
- References
- 0
- FWCI
- 10.89
- Type
- journal article
- Language
- en
- Open access
- closed
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- Yoshikai, N., Mieczkowski, A., Matsumoto, A., Ilies, L., & Nakamura, E. (2010). Iron-Catalyzed C−C Bond Formation at α-Position of Aliphatic Amines via C−H Bond Activation through 1,5-Hydrogen Transfer. Journal of the American Chemical Society. https://doi.org/10.1021/ja100651t
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