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Electron-Transfer Photoredox Catalysis: Development of a Tin-Free Reductive Dehalogenation Reaction
Abstract
We report an operationally simple, tin-free reductive dehalogenation system utilizing the well-known visible-light-activated photoredox catalyst Ru(bpy)(3)Cl(2) in combination with (i)Pr(2)NEt and HCO(2)H or Hantzsch ester as the hydrogen atom donor. Activated C-X bonds may be reduced in good yields with excellent functional-group tolerance and chemoselectivity over aryl and vinyl C-X bonds. The proposed mechanism involves visible-light excitation of the catalyst, which is reduced by the tertiary amine to produce the single-electron reducing agent Ru(bpy)(3)(+). A subsequent single-electron transfer generates the alkyl radical, which is quenched by abstraction of a hydrogen atom. Reductions can be accomplished on a preparative scale with as little as 0.05 mol % Ru catalyst.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Visible light photocatalysis as a greener approach to photochemical synthesis
Yoon, T. P., Ischay, M. A., & Du, J. (2010) · Nature Chemistry · doi:10.1038/nchem.687 · Cited by 2,657
Photoredox Catalysis with Visible Light
Zeitler, K. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904056 · Cited by 991
Control of a Living Radical Polymerization of Methacrylates by Light
Fors, B. P., & Hawker, C. J. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203639 · Cited by 820
Accessing non-natural reactivity by irradiating nicotinamide-dependent enzymes with light
Emmanuel, M. A., Greenberg, N. R., Oblinsky, D. G., & Hyster, T. K. (2016) · Nature · doi:10.1038/nature20569 · Cited by 445
Metadata
- Authors
- Narayanam, J. M. R., Tucker, J. W., & Stephenson, C. R. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-06-05
- Volume
- 131
- Issue
- 25
- Pages
- 8756-8757
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1985066293
- Cited by
- 1,005
- References
- 0
- FWCI
- 22.51
- Type
- journal article
- Language
- en
- Open access
- closed
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- Narayanam, J. M. R., Tucker, J. W., & Stephenson, C. R. J. (2009). Electron-Transfer Photoredox Catalysis: Development of a Tin-Free Reductive Dehalogenation Reaction. Journal of the American Chemical Society. https://doi.org/10.1021/ja9033582
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