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sp3 C−H Bond Arylation Directed by Amidine Protecting Group: α-Arylation of Pyrrolidines and Piperidines
Abstract
A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.
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Cited by
Palladium-catalysed transannular C–H functionalization of alicyclic amines
Topczewski, J. J., Cabrera, P. J., Saper, N. I., & Sanford, M. S. (2016) · Nature · doi:10.1038/nature16957 · Cited by 328
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
Modular, stereocontrolled C β –H/C α –C activation of alkyl carboxylic acids
Shang, M., Feu, K. S., Vantourout, J. C., Barton, L. M., Osswald, H. L., Kato, N., Gagaring, K., McNamara, C. W., Chen, G., Hu, L., et al. (2019) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1903048116 · Cited by 53
Metadata
- Authors
- Pastine, S. J., Gribkov, D. V., & Sames, D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-10-14
- Volume
- 128
- Issue
- 44
- Pages
- 14220-14221
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1985353991
- Cited by
- 313
- References
- 0
- FWCI
- 10.77
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: sp3 C−H Bond Arylation Directed by Amidine Protecting Group: α-Arylation of Pyrrolidines and Piperidines. https://app.cochat.ai/papers/10.1021/ja064481j
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- Pastine, S. J., Gribkov, D. V., & Sames, D. (2006). sp3 C−H Bond Arylation Directed by Amidine Protecting Group: α-Arylation of Pyrrolidines and Piperidines. Journal of the American Chemical Society. https://doi.org/10.1021/ja064481j
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