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Palladium-Catalyzed Amination of Aromatic C−H Bonds with Oxime Esters
Abstract
We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N-O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N-X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.
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Cited by
Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups
Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., & Zhang, Y. (2015) · Organic Chemistry Frontiers · doi:10.1039/c5qo00004a · Cited by 1,533
Predicting reaction performance in C–N cross-coupling using machine learning
Ahneman, D. T., Estrada, J. G., Lin, S., Dreher, S. D., & Doyle, A. G. (2018) · Science · doi:10.1126/science.aar5169 · Cited by 1,058
C–H Activation: Toward Sustainability and Applications
Dalton, T., Faber, T., & Glorius, F. (2021) · ACS Central Science · doi:10.1021/acscentsci.0c01413 · Cited by 833
The Complementary Competitors: Palladium and Copper in C–N Cross-Coupling Reactions
Beletskaya, I. P., & Cheprakov, A. V. (2012) · Organometallics · doi:10.1021/om300683c · Cited by 454
Yu, S., Liu, S., Lan, Y., Wan, B., & Li, X. (2015) · Journal of the American Chemical Society · doi:10.1021/ja511796h · Cited by 331
Oxidizing Directing Groups Enable Efficient and Innovative CH Activation Reactions
Patureau, F. W., & Glorius, F. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201007241 · Cited by 306
Metadata
- Authors
- Tan, Y., & Hartwig, J. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-26
- Volume
- 132
- Issue
- 11
- Pages
- 3676-3677
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2054785509
- Cited by
- 551
- References
- 0
- FWCI
- 28.10
- Type
- journal article
- Language
- en
- Open access
- closed
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