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A New Reagent for Direct Difluoromethylation
Open accessAbstract
Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO(2)CF(2)H)(2), DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated π-systems and thiols. Regiochemical comparisons suggest that the CF(2)H radical generated from the new reagent possesses nucleophilic character.
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Citations
Cited by
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Fujiwara, T., & O’Hagan, D. (2014) · Journal of Fluorine Chemistry · doi:10.1016/j.jfluchem.2014.06.014 · Cited by 894
Tang, X.-J., Thomoson, C. S., & Dolbier, W. R. (2014) · Organic Letters · doi:10.1021/ol502163f · Cited by 323
Recent advances in photoinduced trifluoromethylation and difluoroalkylation
Pan, X., Xia, H., & Wu, J. (2016) · Organic Chemistry Frontiers · doi:10.1039/c6qo00153j · Cited by 283
Papillon, J. P. N., Nakajima, K., Adair, C. D., Hempel, J., Jouk, A. O., Karki, R. G., Mathieu, S., Möbitz, H., Ntaganda, R., Smith, T., et al. (2018) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.8b01318 · Cited by 244
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Robles, O., & Romo, D. (2014) · Nat. Prod. Rep. · doi:10.1039/c3np70087a · Cited by 154
Metadata
- Authors
- Fujiwara, Y., Dixon, J. A., Rodriguez, R. A., Baxter, R. D., Dixon, D. D., Collins, M. R., Blackmond, D. G., & Baran, P. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-01-13
- Volume
- 134
- Issue
- 3
- Pages
- 1494-1497
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2093750721
- Cited by
- 630
- References
- 0
- FWCI
- 33.95
- Type
- journal article
- Language
- en
- Open access
- green
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- Fujiwara, Y., Dixon, J. A., Rodriguez, R. A., Baxter, R. D., Dixon, D. D., Collins, M. R., Blackmond, D. G., & Baran, P. S. (2012). A New Reagent for Direct Difluoromethylation. Journal of the American Chemical Society. https://doi.org/10.1021/ja211422g
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