Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

Shahboz Yakubov and Joshua P. Barham
Beilstein J. Org. Chem. 2020, 16, 2151–2192.

Cite the Following Article

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis
Shahboz Yakubov and Joshua P. Barham
Beilstein J. Org. Chem. 2020, 16, 2151–2192.

How to Cite

Yakubov, S.; Barham, J. P. Beilstein J. Org. Chem. 2020, 16, 2151–2192. doi:10.3762/bjoc.16.183

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 11.2 MB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Ge, R.; Xu, Z.; Yang, K.; Ge, H. Transition-metal-catalyzed C(sp3)–H bond fluorination reactions. Chem Catalysis 2024, 101009. doi:10.1016/j.checat.2024.101009
  • Li, W.; Li, Z.; Zhong, D.; Wang, N.; Li, H. Photoinduced Perfluoroalkyloximation of Alkenes with Simple Perfluoroalkyl Halides. Chinese Journal of Chemistry 2024. doi:10.1002/cjoc.202400181
  • Das, A.; Justin Thomas, K. R. Generation and Application of Aryl Radicals Under Photoinduced Conditions. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202400193. doi:10.1002/chem.202400193
  • Lu, X.; Wang, X.; Chen, S.; Fan, T.; Zhao, L.; Zhong, R.; Sun, G. The rat acute oral toxicity of trifluoromethyl compounds (TFMs): a computational toxicology study combining the 2D-QSTR, read-across and consensus modeling methods. Archives of toxicology 2024. doi:10.1007/s00204-024-03739-w
  • Parsons, A. F.; Parsons, T. F. doi:10.1002/9781119716846.ch13
  • Zhu, W. F.; Empel, C.; Pelliccia, S.; Koenigs, R. M.; Proschak, E.; Hernandez-Olmos, V. Photochemistry in Medicinal Chemistry and Chemical Biology. Journal of medicinal chemistry 2024, 67, 4322–4345. doi:10.1021/acs.jmedchem.3c02109
  • Das, A.; Gouthaman, S.; Justin Thomas, K. R. Photocatalysis as a green alternative toolkit for the construction of nitrogen-enriched heterocycles via the direct and indirect activation of alkynes/alkenes. Green Chemistry 2024, 26, 1223–1280. doi:10.1039/d3gc03971d
  • Atkins, A. P.; Chaturvedi, A. K.; Tate, J. A.; Lennox, A. J. J. Pulsed electrolysis: enhancing primary benzylic C(sp3)-H nucleophilic fluorination. Organic chemistry frontiers : an international journal of organic chemistry 2024, 11, 802–808. doi:10.1039/d3qo01865b
  • Tian, X.; Liu, Y.; Yakubov, S.; Schütte, J.; Chiba, S.; Barham, J. P. Photo- and electro-chemical strategies for the activations of strong chemical bonds. Chemical Society reviews 2024, 53, 263–316. doi:10.1039/d2cs00581f
  • Chen, Z.; Zhu, W.; Wang, C.; Xu, N.; Jin, Q.; Huang, X.; Song, S.; Li, J. Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer. Organic Chemistry Frontiers 2023, 10, 4709–4717. doi:10.1039/d3qo00931a
  • Thomas, R. P.; Grant, E. K.; Dickinson, E. R.; Zappacosta, F.; Edwards, L. J.; Hann, M. M.; House, D.; Tomkinson, N. C. O.; Bush, J. T. Reactive fragments targeting carboxylate residues employing direct to biology, high-throughput chemistry. RSC medicinal chemistry 2023, 14, 671–679. doi:10.1039/d2md00453d
  • Dolna, M.; Narodowiec, J.; Staszewska-Krajewska, O.; Szcześniak, P.; Furman, B. Remotely controlled flow photo-Fries-type rearrangement of N-vinylazetidinones: an efficient route to structurally diverse 2,3-dihydro-4-pyridones. Reaction Chemistry & Engineering 2023, 8, 784–789. doi:10.1039/d2re00438k
  • Castiello, C.; Junghanns, P.; Mergel, A.; Jacob, C.; Ducho, C.; Valente, S.; Rotili, D.; Fioravanti, R.; Zwergel, C.; Mai, A. GreenMedChem: the challenge in the next decade toward eco-friendly compounds and processes in drug design. Green Chemistry 2023, 25, 2109–2169. doi:10.1039/d2gc03772f
  • Das, A.; Justin Thomas, K. R. Deconstruction of electron-deficient alkenes to carbonyl constituents by light-induced hydrogen atom transfer. Green Chemistry 2023, 25, 1078–1084. doi:10.1039/d2gc04424b
  • Yamashita, K.; Fujiwara, Y.; Hamashima, Y. Amide-Ligand-Promoted Silver-Catalyzed C-H Fluorination via Radical/Polar Crossover. The Journal of organic chemistry 2023, 88, 1865–1874. doi:10.1021/acs.joc.2c02575
  • Kliś, T. Visible-Light Photoredox Catalysis for the Synthesis of Fluorinated Aromatic Compounds. Catalysts 2023, 13, 94. doi:10.3390/catal13010094
  • Mandal, A.; Jang, J.; Yang, B.; Kim, H.; Shin, K. Palladium-Catalyzed Electrooxidative Hydrofluorination of Aryl-Substituted Alkenes with a Nucleophilic Fluorine Source. Organic letters 2022, 25, 195–199. doi:10.1021/acs.orglett.2c04045
  • Yakubov, S.; Stockerl, W. J.; Tian, X.; Shahin, A.; Mandigma, M. J. P.; Gschwind, R. M.; Barham, J. P. Benzoates as photosensitization catalysts and auxiliaries in efficient, practical, light-powered direct C(sp3)-H fluorinations. Chemical science 2022, 13, 14041–14051. doi:10.1039/d2sc05735b
  • Yang, Y.; Shen, Q. doi:10.1002/9783527834242.chf0177
  • Dong, L.; Wang, X.; Nie, Y.; Yu, S.; Li, H.; Zhao, Q.; Fan, Z.; Wang, Y.; Tan, X.; Yu, Z. Regioselective Perfluoroalkylation of 4‐Quinolones Using Sodium Perfluoroalkyl Sulfinates. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200842
Other Beilstein-Institut Open Science Activities