The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology
Abstract
We present here a reassessment of our transition-metal free Suzuki-type coupling protocol. We believe that, although the reaction can be run without the need for addition of a metal catalyst, palladium contaminants down to a level of 50 ppb found in commercially available sodium carbonate are responsible for the generation of the biaryl rather than, as previously suggested, an alternative non-palladium-mediated pathway. We present a revised methodology for Suzuki couplings using ultralow palladium concentrations for use with aryl and vinyl boronic acids and discuss the effects of the purity of the boronic acid on the reaction.
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Cites
Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction
Hassan, J., Sévignon, M., Gozzi, C., Schulz, E., & Lemaire, M. (2002) · Chemical Reviews · doi:10.1021/cr000664r · Cited by 3,663
Perreux, L., & Loupy, A. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00905-x · Cited by 1,288
de Vries, A. H. M., Mulders, J. M. C. A., Mommers, J. H. M., Henderickx, H. J. W., & de Vries, J. G. (2003) · Organic Letters · doi:10.1021/ol035184b · Cited by 551
Copper-Catalyzed Suzuki Cross-Coupling Using Mixed Nanocluster Catalysts
Thathagar, M. B., Beckers, J., & Rothenberg, G. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027716+ · Cited by 301
Pröckl, S. S., Kleist, W., Gruber, M. A., & Köhler, K. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200353473 · Cited by 260
Miao, W., & Chan, T. H. (2003) · Organic Letters · doi:10.1021/ol035977y · Cited by 157
Biaryls via Suzuki Cross-Couplings Catalyzed by Nickel on Charcoal
Lipshutz, B. H., Sclafani, J. A., & Blomgren, P. A. (2000) · Tetrahedron · doi:10.1016/s0040-4020(99)01096-0 · Cited by 120
Arcadi, A., Cerichelli, G., Chiarini, M., Correa, N. M., & Zorzan, D. H. (2003) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200300356 · Cited by 117
Smith, M. D., Stepan, A. F., Ramarao, C., Brennan, P. E., & Ley, S. V. (2003) · Chemical Communications · doi:10.1039/b308465e · Cited by 85
Platinum Catalysts for Suzuki Biaryl Coupling Reactions
Bedford, R. B., Hazelwood, S. L., & Albisson, D. A. (2002) · Organometallics · doi:10.1021/om0202524 · Cited by 63
Cited by
Cross‐Coupling Reactions Of Organoboranes: An Easy Way To Construct CC Bonds (Nobel Lecture)
Suzuki, A. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201101379 · Cited by 2,055
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
Schuster, O., Yang, L., Raubenheimer, H. G., & Albrecht, M. (2009) · Chemical Reviews · doi:10.1021/cr8005087 · Cited by 1,074
Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions
Molnár, Á. (2011) · Chemical Reviews · doi:10.1021/cr100355b · Cited by 1,042
Metadata
- Authors
- Arvela, R. K., Leadbeater, N. E., Sangi, M. S., Williams, V. A., Granados, P., & Singer, R. D.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-12-08
- Volume
- 70
- Issue
- 1
- Pages
- 161-168
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2950703442
- Cited by
- 384
- References
- 12
- FWCI
- 13.77
- Type
- journal article
- Language
- en
- Open access
- closed
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- Arvela, R. K., Leadbeater, N. E., Sangi, M. S., Williams, V. A., Granados, P., & Singer, R. D. (2005). A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology. The Journal of Organic Chemistry. https://doi.org/10.1021/jo048531j
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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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