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A Catalytic Probe of the Surface of Colloidal Palladium Particles Using Heck Coupling Reactions
Abstract
A series of well-defined homopolymer-stabilized Pd colloids with varying metal particle size was used to study the Heck coupling reaction between aryl halides and olefins. Correlation of initial reaction rates and particle sizes determined by transmission electron microscopy demonstrates that the Heck reaction is a sensitive probe of metal surface structure. The presence of the colloid-stabilizing homopolymer affords a much more stable catalyst than that obtained using the colloid−precursor metal complexes alone. Extremely high total turnover numbers (TON, moles of substrate/moles of Pd; TON = 100 000) and turnover frequencies (TOF = TON/h; TOF > 80 000) are easily attainable with poly(vinylpyrrolidone)-stabilized colloidal palladium in the coupling of p -bromobenzaldehyde with butyl acrylate.
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Cited by
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Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts
Yin, & Liebscher, J. (2007) · Chemical Reviews · doi:10.1021/cr0505674 · Cited by 2,085
Phan, N. T. S., Van Der Sluys, M., & Jones, C. W. (2006) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200505473 · Cited by 1,905
The Mechanisms of the Stille Reaction
Espinet, P., & Echavarren, A. M. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200300638 · Cited by 959
Mori, K., Hara, T., Mizugaki, T., Ebitani, K., & Kaneda, K. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0488683 · Cited by 939
Chowdhury, S., Mohan, R. S., & Scott, J. L. (2007) · Tetrahedron · doi:10.1016/j.tet.2006.11.001 · Cited by 593
Ott, L. S., & Finke, R. G. (2007) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2006.08.016 · Cited by 454
Suzuki Cross-Coupling Reactions Catalyzed by Palladium Nanoparticles in Aqueous Solution
Li, Y., Hong, X. M., Collard, D. M., & El-Sayed, M. A. (2000) · Organic Letters · doi:10.1021/ol0061687 · Cited by 447
Li, Y., & El-Sayed, M. A. (2001) · The Journal of Physical Chemistry B · doi:10.1021/jp010904m · Cited by 441
Astruc, D., Lu, F., & Aranzaes, J. R. (2005) · Angewandte Chemie · doi:10.1002/ange.200500766 · Cited by 417
Selvakannan, P., Swami, A., Srisathiyanarayanan, D., Shirude, P. S., Pasricha, R., Mandale, A. B., & Sastry, M. (2004) · Langmuir · doi:10.1021/la049258j · Cited by 377
Semagina, N., & Kiwi‐Minsker, L. (2009) · Catalysis Reviews · doi:10.1080/01614940802480379 · Cited by 181
Metadata
- Authors
- Le Bars, J., Specht, U., Bradley, J. S., & Blackmond, D. G.
- Venue
- Langmuir
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-08-26
- Volume
- 15
- Issue
- 22
- Pages
- 7621-7625
- ISSN
- 0743-7463 (ISSN-L)
- 1520-5827
- OpenAlex
- W2042175392
- Cited by
- 276
- References
- 0
- FWCI
- 9.83
- Type
- journal article
- Language
- en
- Open access
- closed
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