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Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents
Open accessAbstract
The reaction of aryl halides with secondary amines in the presence of silylamide base and tri-o-tolyphopshine palladium complexes gives arylamine products. This process provides a convenient method for performing these hetero-cross coupling reactions without the necessity for forming tin amides and disposing of tin halides. This reaction follows from a mechanistic analysis of the coupling reaction with tin amides and occurs as a result of the cleavage of palladium aryl halide dimers with secondary amines.
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Cited by
Bang-Andersen, B., Ruhland, T., Jørgensen, M., Smith, G., Frederiksen, K., Jensen, K. G., Zhong, H., Nielsen, S. M., Hogg, S., Mørk, A., et al. (2011) · Journal of Medicinal Chemistry · doi:10.1021/jm101459g · Cited by 606
Palladiumkatalysierte Kreuzkupplungen: eine historische Perspektive im Kontext der Nobel‐Preise 2010
Johansson Seechurn, C. C. C., Kitching, M. O., Colacot, T. J., & Snieckus, V. (2012) · Angewandte Chemie · doi:10.1002/ange.201107017 · Cited by 499
Scope and Limitations of the Pd/BINAP-Catalyzed Amination of Aryl Bromides
Wolfe, J. P., & Buchwald, S. L. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo9916986 · Cited by 438
Intramolecular five-membered ring compounds and their applications
Omae, I. (2004) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2004.05.011 · Cited by 288
Metadata
- Authors
- Louie, J., & Hartwig, J. F.
- Venue
- Tetrahedron Letters
- Publisher
- Elsevier BV
- Published
- 1995-05
- Volume
- 36
- Issue
- 21
- Pages
- 3609-3612
- ISSN
- 0040-4039 (ISSN-L)
- OpenAlex
- W1993847723
- Cited by
- 914
- References
- 0
- FWCI
- 26.29
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- CoChat. (2026). Citation check: Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents. https://app.cochat.ai/papers/10.1016/0040-4039(95)00605-c
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- Louie, J., & Hartwig, J. F. (1995). Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents. Tetrahedron Letters. https://doi.org/10.1016/0040-4039(95)00605-c
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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