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Copper Catalyzed C(sp3)–H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer
Open accessAbstract
Utilizing catalytic CuCl 2 we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp 3 )–H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp 3 )–H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation of a highly active HAT reagent in an operationally simple and atom economical protocol.
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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
Photocatalytic Late-Stage C–H Functionalization
Bellotti, P., Huang, H.-M., Faber, T., & Glorius, F. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00478 · Cited by 623
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Self-citationChemical Upcycling of Commercial Polystyrene via Catalyst-Controlled Photooxidation
Oh, S., & Stache, E. E. (2022) · Journal of the American Chemical Society · doi:10.1021/jacs.2c01411 · Cited by 361
Metadata
- Authors
- Treacy, S. M., & Rovis, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2021-02-12
- Volume
- 143
- Issue
- 7
- Pages
- 2729-2735
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W3126592395
- Cited by
- 314
- References
- 1
- FWCI
- 20.53
- Type
- journal article
- Language
- en
- Open access
- green
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