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Silicates as Latent Alkyl Radical Precursors: Visible‐Light Photocatalytic Oxidation of Hypervalent Bis‐Catecholato Silicon Compounds
Abstract
This works introduces hypervalent bis‐catecholato silicon compounds as versatile sources of alkyl radicals upon visible‐light photocatalysis. Using Ir[(dF(CF 3)ppy)2(bpy)](PF 6) (dF(CF 3)ppy=2‐(2,4‐difluorophenyl)‐5‐trifluoromethylpyridine, bpy=bipyridine) as catalytic photooxidant, a series of alkyl radicals, including highly reactive primary ones can be generated and engaged in various intermolecular homolytic reactions. Based on cyclic voltammetry, Stern–Volmer studies, and supported by calculations, a mechanism involving a single‐electron transfer from the silicate to the photoactivated iridium complex has been proposed. This oxidative photocatalyzed process can be efficiently merged with nickel‐catalyzed CC cross‐coupling reactions.
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Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations
Heitz, D. R., Tellis, J. C., & Molander, G. A. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b04789 · Cited by 518
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Metadata
- Authors
- Corcé, V., Chamoreau, L., Derat, E., Goddard, J., Ollivier, C., & Fensterbank, L.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2015-07-24
- Volume
- 54
- Issue
- 39
- Pages
- 11414-11418
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2168711912
- Cited by
- 311
- References
- 1
- FWCI
- 13.64
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Silicates as Latent Alkyl Radical Precursors: Visible‐Light Photocatalytic Oxidation of Hypervalent Bis‐Catecholato Silicon Compounds. https://app.cochat.ai/papers/10.1002/anie.201504963
- The paper
- Corcé, V., Chamoreau, L., Derat, E., Goddard, J., Ollivier, C., & Fensterbank, L. (2015). Silicates as Latent Alkyl Radical Precursors: Visible‐Light Photocatalytic Oxidation of Hypervalent Bis‐Catecholato Silicon Compounds. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201504963
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