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Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis
Open accessAbstract
Using nickel and photoredox catalysis, the direct functionalization of C(sp 3)−H bonds of N‐aryl amines by acyl electrophiles is described. The method affords a diverse range of α‐amino ketones at room temperature and is amenable to late‐stage coupling of complex and biologically relevant groups. C(sp 3)−H activation occurs by photoredox‐mediated oxidation to generate α‐amino radicals which are intercepted by nickel in catalytic C(sp 3)−C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross‐coupling while avoiding limitations commonly associated with transition‐metal‐mediated C(sp 3)−H activation, including requirements for chelating directing groups and high reaction temperatures.
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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
Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)‐Catalyzed C−H Alkylation of Azacycles
Tran, A. T., & Yu, J. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201704755 · Cited by 105
Metadata
- Authors
- Joe, C. L., & Doyle, A. G.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2016-02-17
- Volume
- 55
- Issue
- 12
- Pages
- 4040-4043
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2273976432
- Cited by
- 267
- References
- 1
- FWCI
- 14.85
- Type
- journal article
- Language
- en
- Open access
- green
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