The DOI matches its Crossref record; 20 of the 20 references it cites were found in a registry or an index.
Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature
Abstract
The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination.
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Cites
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Cited by
Circular olefin copolymers made de novo from ethylene and α-olefins
Han, X.-W., Zhang, X., Zhou, Y., Maimaitiming, A., Sun, X.-L., Gao, Y., Li, P., Zhu, B., Chen, E. Y.-X., Kuang, X., et al. (2024) · Nature Communications · doi:10.1038/s41467-024-45219-w · Cited by 85
Metadata
- Authors
- Wang, G.-Z., Shang, R., Cheng, W.-M., & Fu, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-11-20
- Volume
- 139
- Issue
- 50
- Pages
- 18307-18312
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2767672561
- Cited by
- 341
- References
- 20
- FWCI
- 13.82
- Type
- journal article
- Language
- en
- Open access
- closed
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