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Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates
Open accessAbstract
Single-electron transmetalation is recognized as an enabling technology for the mild transfer of alkyl groups to transition metal catalysts in cross-coupling reactions. Hypercoordinate silicates represent a new and improved class of radical precursors because of their low oxidation potentials and the innocuous byproducts generated upon oxidation. Herein, we report the cross-coupling of secondary and primary ammonium alkylsilicates with (hetero)aryl bromides in good to excellent yields. The base-free conditions have exceptional protic group tolerance on both partners, permitting the cross-coupling of unprotected primary and secondary amines.
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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
Privileged scaffolds for library design and drug discovery
Welsch, M. E., Snyder, S. A., & Stockwell, B. R. (2010) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2010.02.018 · Cited by 1,509
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
Self-citationTay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Metadata
- Authors
- Jouffroy, M., Primer, D. N., & Molander, G. A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-12-24
- Volume
- 138
- Issue
- 2
- Pages
- 475-478
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2218141500
- Cited by
- 288
- References
- 2
- FWCI
- 17.08
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Jouffroy, M., Primer, D. N., & Molander, G. A. (2016). Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.5b10963
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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