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Highly Active Thermomorphic Fluorous Palladacycle Catalyst Precursors for the Heck Reaction; Evidence for a Palladium Nanoparticle Pathway
Abstract
[reaction: see text] The fluorous Schiff base p-Rf8(CH2)3C6H4C(=N(CH2)3Rf8)(CH2)2Rf8 (Rf8 = n-C8F17) is prepared in six steps from p-iodobenzaldehyde and then cyclopalladated (Pd(OAc)2) to give highly effective catalyst precursors for Heck reactions, conducted under homogeneous conditions (DMF, 80-140 degrees C, turnover numbers >10(6)) in the absence of fluorous solvents. Rate, recycling, and other data suggest that the palladacycles serve as sources of palladium nanoparticles, which are the dominant active catalysts.
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Citations
Cited by
Nanoparticles as Recyclable Catalysts: The Frontier between Homogeneous and Heterogeneous Catalysis
Astruc, D., Lu, F., & Aranzaes, J. R. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500766 · Cited by 3,131
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 Potential of Palladacycles: More Than Just Precatalysts
Dupont, J., Consorti, C. S., & Spencer, J. (2005) · Chemical Reviews · doi:10.1021/cr030681r · Cited by 1,300
Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions
Molnár, Á. (2011) · Chemical Reviews · doi:10.1021/cr100355b · Cited by 1,042
de Vries, J. G. (2006) · Dalton Trans. · doi:10.1039/b506276b · Cited by 624
Metadata
- Authors
- Rocaboy, C., & Gladysz, J. A.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-22
- Volume
- 4
- Issue
- 12
- Pages
- 1993-1996
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W1973072968
- Cited by
- 176
- References
- 0
- FWCI
- 14.42
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Highly Active Thermomorphic Fluorous Palladacycle Catalyst Precursors for the Heck Reaction; Evidence for a Palladium Nanoparticle Pathway. https://app.cochat.ai/papers/10.1021/ol025790r
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- Rocaboy, C., & Gladysz, J. A. (2002). Highly Active Thermomorphic Fluorous Palladacycle Catalyst Precursors for the Heck Reaction; Evidence for a Palladium Nanoparticle Pathway. Organic Letters. https://doi.org/10.1021/ol025790r
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