The DOI matches its Crossref record; 22 of the 22 references it cites were found in a registry or an index.
Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay
Open accessAbstract
Direct methods for stereoselective functionalization of sp 3 -hybridized carbon–hydrogen [C(sp 3 )–H] bonds in complex organic molecules could facilitate much more efficient preparation of therapeutics and agrochemicals. Here, we report a copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C–H bonds into benzylic nitriles. Hydrogen-atom abstraction affords an achiral benzylic radical that undergoes asymmetric C(sp 3 )–CN bond formation upon reaction with a chiral copper catalyst. The reactions proceed efficiently at room temperature with the benzylic substrate as limiting reagent, exhibit broad substrate scope with high enantioselectivity (typically 90 to 99% enantiomeric excess), and afford products that are key precursors to important bioactive molecules. Mechanistic studies provide evidence for diffusible organic radicals and highlight the difference between these reactions and C–H oxidations mediated by enzymes and other catalysts that operate via radical rebound pathways.
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Cites
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Mechanism of Oxidation Reactions Catalyzed by Cytochrome P450 Enzymes
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Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion
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Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore
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Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp 3 -carbons with aryl halides
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Self-citationA Predictably Selective Aliphatic C–H Oxidation Reaction for Complex Molecule Synthesis
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Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
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Cited by
Electrochemical Late-Stage Functionalization
Wang, Y., Dana, S., Long, H., Xu, Y., Li, Y., Kaplaneris, N., & Ackermann, L. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.3c00158 · Cited by 361
Wang, D., Zhu, N., Chen, P., Lin, Z., & Liu, G. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b09802 · Cited by 304
Self-citationTang, Q., Zhao, L., Xie, J., Liu, K., Liu, W., & Zhou, S. (2019) · Chirality · doi:10.1002/chir.23072 · Cited by 10
Metadata
- Authors
- Zhang, W., Wang, F., McCann, S. D., Wang, D., Chen, P., Stahl, S. S., & Liu, G.
- Venue
- Science
- Published
- 2016-09-02
- Volume
- 353
- Issue
- 6303
- Pages
- 1014-1018
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2515068481
- Cited by
- 676
- References
- 22
- FWCI
- 27.77
- Type
- journal article
- Language
- en
- Open access
- green
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- Zhang, W., Wang, F., McCann, S. D., Wang, D., Chen, P., Stahl, S. S., & Liu, G. (2016). Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay. Science. https://doi.org/10.1126/science.aaf7783
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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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