The DOI matches its Crossref record; 33 of the 33 references it cites were found in a registry or an index.
Practical and regioselective amination of arenes using alkyl amines
Open accessAbstract
The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.The synthesis of aryl amines is traditionally achieved through aromatic nitration or transition metal-catalysed cross coupling. Now, photocatalysis provides a route for the direct and selective C–H amination of aromatics with alkyl amines, without the need for pre-functionalization. This reaction tolerates a variety of functional groups and can be used for late-stage modification.
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Cited by
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Late-stage C–H functionalization offers new opportunities in drug discovery
Guillemard, L., Kaplaneris, N., Ackermann, L., & Johansson, M. J. (2021) · Nature Reviews Chemistry · doi:10.1038/s41570-021-00300-6 · Cited by 837
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
Motiwala, H. F., Armaly, A. M., Cacioppo, J. G., Coombs, T. C., Koehn, K. R. K., Norwood, V. M., & Aubé, J. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00749 · Cited by 593
Photocatalysis in the Life Science Industry
Candish, L., Collins, K. D., Cook, G. C., Douglas, J. J., Gómez-Suárez, A., Jolit, A., & Keess, S. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00416 · Cited by 428
Self-citation
Metadata
- Authors
- Ruffoni, A., Juliá, F., Svejstrup, T. D., McMillan, A. J., Douglas, J. J., & Leonori, D.
- Venue
- Nature Chemistry
- Published
- 2019-04-22
- Volume
- 11
- Issue
- 5
- Pages
- 426-433
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- OpenAlex
- W2935710415
- Cited by
- 257
- References
- 33
- FWCI
- 14.09
- Type
- journal article
- Language
- en
- Open access
- green
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- Ruffoni, A., Juliá, F., Svejstrup, T. D., McMillan, A. J., Douglas, J. J., & Leonori, D. (2019). Practical and regioselective amination of arenes using alkyl amines. Nature Chemistry. https://doi.org/10.1038/s41557-019-0254-5
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