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Friedel–Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis
Open accessAbstract
Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S(2)O(8)(2-)) in the presence of the visible light catalyst, Ru(bpy)(3)Cl(2), at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.
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Cited by
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Xi, Y., Yi, H., & Lei, A. (2013) · Organic & Biomolecular Chemistry · doi:10.1039/c3ob40137e · Cited by 658
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Bergonzini, G., Schindler, C. S., Wallentin, C.-J., Jacobsen, E. N., & Stephenson, C. R. J. (2014) · Chem. Sci. · doi:10.1039/c3sc52265b · Cited by 277
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Metadata
- Authors
- Dai, C., Meschini, F., Narayanam, J. M. R., & Stephenson, C. R. J.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-04-18
- Volume
- 77
- Issue
- 9
- Pages
- 4425-4431
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2085513121
- Cited by
- 212
- References
- 0
- FWCI
- 8.46
- Type
- journal article
- Language
- en
- Open access
- green
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