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Highly Active Palladium Catalysts for Suzuki Coupling Reactions
Abstract
Mixtures of palladium acetate and o -(di- tert -butylphosphino)biphenyl ( 4 ) catalyze the room-temperature Suzuki coupling of aryl bromides and aryl chlorides with 0.5−1.0 mol % Pd. Use of o -(dicyclohexylphosphino)biphenyl ( 2 ) allows Suzuki couplings to be carried out at low catalyst loadings (0.000001−0.02 mol % Pd). The process tolerates a broad range of functional groups and substrate combinations including the use of sterically hindered substrates. This is the most active catalyst system in terms of reaction temperature, turnover number, and steric tolerance which has been reported to date.
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Cited by
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Johansson Seechurn, C. C. C., Kitching, M. O., Colacot, T. J., & Snieckus, V. (2012) · Angewandte Chemie · doi:10.1002/ange.201107017 · Cited by 499
Li, Y., & El-Sayed, M. A. (2001) · The Journal of Physical Chemistry B · doi:10.1021/jp010904m · Cited by 441
Catalyzed Asymmetric Arylation Reactions
Bolm, C., Hildebrand, J. P., Muñiz, K., & Hermanns, N. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20010917)40:18<3284::aid-anie3284>3.0.co;2-u · Cited by 309
Primo, A., Liebel, M., & Quignard, F. (2009) · Chemistry of Materials · doi:10.1021/cm8020337 · Cited by 107
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Ding, K., Zannat, F., Morris, J. C., Brennessel, W. W., & Holland, P. L. (2009) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2009.09.005 · Cited by 52
Metadata
- Authors
- Wolfe, J. P., Singer, R. A., Yang, B. H., & Buchwald, S. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-10-01
- Volume
- 121
- Issue
- 41
- Pages
- 9550-9561
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1997159316
- Cited by
- 1,132
- References
- 0
- FWCI
- 45.75
- Type
- journal article
- Language
- en
- Open access
- closed
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- Wolfe, J. P., Singer, R. A., Yang, B. H., & Buchwald, S. L. (1999). Highly Active Palladium Catalysts for Suzuki Coupling Reactions. Journal of the American Chemical Society. https://doi.org/10.1021/ja992130h
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
