The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions
Abstract
In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to give the corresponding aryl sulfides in excellent yield. The reaction is useful to prepare symmetrical or unsymmetrical diaryl sulfides and aryl alkyl sulfides. The reaction mechanism does not involve aryl halide radical anions, but is thought to involve oxidative addition of aryl halide to Pd(0), nucleophilic substitution on the adduct followed by reductive elimination.
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Citations
Cites
Tamao, K., Sumitani, K., & Kumada, M. (1972) · Journal of the American Chemical Society · doi:10.1021/ja00767a075 · Cited by 1,291
Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives
Dieck, H. A., & HECK, F. R. (1975) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(00)94049-x · Cited by 749
Nucleophilic reactivity constants toward methyl iodide and trans-dichlorodi(pyridine)platinum(II)
Pearson, R. G., Sobel, H. R., & Songstad, J. (1968) · Journal of the American Chemical Society · doi:10.1021/ja01004a021 · Cited by 455
Cited by
Transition‐Metal‐Catalyzed CS Bond Coupling Reaction
Lee, C., Liu, Y., & Badsara, S. S. (2014) · Chemistry – An Asian Journal · doi:10.1002/asia.201301500 · Cited by 477
Arylation Chemistry for Bioconjugation
Zhang, C., Vinogradova, E. V., Spokoyny, A. M., Buchwald, S. L., & Pentelute, B. L. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201806009 · Cited by 265
Metadata
- Authors
- Migita, T., Shimizu, T., Asami, Y., Shiobara, J.-I., Kato, Y., & Kosugi, M.
- Venue
- Bulletin of the Chemical Society of Japan
- Publisher
- Oxford University Press (OUP)
- Published
- 1980-05-01
- Volume
- 53
- Issue
- 5
- Pages
- 1385-1389
- ISSN
- 0009-2673 (ISSN-L)
- 1348-0634
- OpenAlex
- W2038413024
- Cited by
- 411
- References
- 3
- FWCI
- 6.06
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions. https://app.cochat.ai/papers/10.1246/bcsj.53.1385
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- Migita, T., Shimizu, T., Asami, Y., Shiobara, J.-I., Kato, Y., & Kosugi, M. (1980). The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions. Bulletin of the Chemical Society of Japan. https://doi.org/10.1246/bcsj.53.1385
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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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