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

  • 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
  • Leguizamon, S. C.; Monk, N. T.; Hochrein, M. T.; Zapien, E. M.; Yoon, A.; Foster, J. C.; Appelhans, L. N. Photoinitiated Olefin Metathesis and Stereolithographic Printing of Polydicyclopentadiene. Macromolecules 2022, 55, 8273–8282. doi:10.1021/acs.macromol.2c01244
  • Kim, S.; Hwang, K. H.; Park, H. G.; Kwak, J.; Lee, H.; Kim, H. Radical hydrodifluoromethylation of unsaturated C-C bonds via an electroreductively triggered two-pronged approach. Communications chemistry 2022, 5, 96. doi:10.1038/s42004-022-00697-1
  • Tian, X.; Kaur, J.; Yakubov, S.; Barham, J. P. α-Amino Radical Halogen Atom Transfer Agents for Metallaphotoredox-Catalyzed Cross-Electrophile Couplings of Distinct Organic Halides. ChemSusChem 2022, 15, e202200906. doi:10.1002/cssc.202200906
  • Shen, G.-B.; Yu, H.-Y.; Xu, Z.; Cao, W.; Liu, J.; Xie, L.; Yan, M. Theoretical study for evaluating and discovering organic hydride compounds as novel trifluoromethylation reagents. Organic & biomolecular chemistry 2022, 20, 2831–2842. doi:10.1039/d2ob00056c
  • Wu, S.; Kaur, J.; Karl, T. A.; Tian, X.; Barham, J. P. Synthetische molekulare Photoelektrochemie: neue synthetische Anwendungen, mechanistische Einblicke und Möglichkeiten zur Skalierung. Angewandte Chemie 2022, 134. doi:10.1002/ange.202107811
  • Wu, S.; Kaur, J.; Karl, T. A.; Tian, X.; Barham, J. P. Synthetic Molecular Photoelectrochemistry: New Frontiers in Synthetic Applications, Mechanistic Insights and Scalability. Angewandte Chemie (International ed. in English) 2022, 61, e202107811. doi:10.1002/anie.202107811
  • Kawamoto, T.; Kawabata, T.; Noguchi, K.; Kamimura, A. Vicinal Difunctionalization of Alkenes Using Vinyl Triflates Leading to γ-Trifluoromethylated Ketones. Organic letters 2021, 24, 324–327. doi:10.1021/acs.orglett.1c03988
  • Muralirajan, K.; Kancherla, R.; Bau, J. A.; Taksande, M. R.; Qureshi, M.; Takanabe, K.; Rueping, M. Exploring the Structure and Performance of Cd–Chalcogenide Photocatalysts in Selective Trifluoromethylation. ACS Catalysis 2021, 11, 14772–14780. doi:10.1021/acscatal.1c04053
  • Tian, X.; Karl, T. A.; Reiter, S.; Yakubov, S.; de Vivie-Riedle, R.; König, B.; Barham, J. P. Electro-mediated PhotoRedox Catalysis for Selective C(sp3)-O Cleavages of Phosphinated Alcohols to Carbanions. Angewandte Chemie (International ed. in English) 2021, 60, 20817–20825. doi:10.1002/anie.202105895
Other Beilstein-Institut Open Science Activities