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Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts
Abstract
Herein, the development of visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [Ir{dF(CF(3))ppy}(2)(dtbbpy)]PF(6) and [Ru(bpy)(3)]Cl(2) is presented. Initial investigations indicated that the oxidative quenching of photocatalysts could effectively be utilized for ATRA, and since that report, the protocol has been expanded by broadening the scope of the reaction in terms of the photocatalysts, substrates, and solvents. In addition, further modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy)(3)]Cl(2) with sodium ascorbate as the sacrificial electron donor. These results signify the complementary nature of the oxidative and reductive quenching pathways of photocatalysts and the ability to predictably direct reaction outcome through modification of the reaction conditions.
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Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Photoactive Chiral Metal–Organic Frameworks for Light-Driven Asymmetric α-Alkylation of Aldehydes
Wu, P., He, C., Wang, J., Peng, X., Li, X., An, Y., & Duan, C. (2012) · Journal of the American Chemical Society · doi:10.1021/ja305367j · Cited by 445
Tang, X.-J., Thomoson, C. S., & Dolbier, W. R. (2014) · Organic Letters · doi:10.1021/ol502163f · Cited by 323
Metadata
- Authors
- Wallentin, C.-J., Nguyen, J. D., Finkbeiner, P., & Stephenson, C. R. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-05-16
- Volume
- 134
- Issue
- 21
- Pages
- 8875-8884
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2331533611
- Cited by
- 969
- References
- 0
- FWCI
- 34.27
- Type
- journal article
- Language
- en
- Open access
- closed
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- Wallentin, C.-J., Nguyen, J. D., Finkbeiner, P., & Stephenson, C. R. J. (2012). Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts. Journal of the American Chemical Society. https://doi.org/10.1021/ja300798k
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