N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

Scholarly Works

• Mentzel, P.; Holzapfel, M.; Schmiedel, A.; Günther, J.; Michel, M.; Krummenacher, I.; Wodyński, A.; Kaupp, M.; Braunschweig, H.; Lambert, C. Structure and Photophysics of N-Tolanyl-phenochalcogenazines and their Radical Cations. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, e202303782. doi:10.1002/chem.202303782
• Zhang, B.; Li, T.-T.; Mao, Z.-C.; Jiang, M.; Zhang, Z.; Zhao, K.; Qu, W.-Y.; Xiao, W.-J.; Chen, J.-R. Enantioselective Cyanofunctionalization of Aromatic Alkenes via Radical Anions. Journal of the American Chemical Society 2024, 146, 1410–1422. doi:10.1021/jacs.3c10439
• 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
• Weick, F.; Hagmeyer, N.; Giraud, M.; Dietzek-Ivanšić, B.; Wagenknecht, H.-A. Reductive Activation of Aryl Chlorides by Tuning the Radical Cation Properties of N-Phenylphenothiazines as Organophotoredox Catalysts. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302347. doi:10.1002/chem.202302347
• Halder, S.; Mandal, S.; Kundu, A.; Mandal, B.; Adhikari, D. Super-Reducing Behavior of Benzo[b]phenothiazine Anion Under Visible-Light Photoredox Condition. Journal of the American Chemical Society 2023, 145, 22403–22412. doi:10.1021/jacs.3c05787
• Mehrotra, R. N. doi:10.1002/9781119608288.ch3
• Wang, R.; Gao, L.; Zhou, C.; Zhang, X. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers. Chinese Journal of Organic Chemistry 2023, 43, 1136. doi:10.6023/cjoc202211013
• Noto, N.; Saito, S. Arylamines as More Strongly Reducing Organic Photoredox Catalysts than fac-[Ir(ppy)3]. ACS Catalysis 2022, 12, 15400–15415. doi:10.1021/acscatal.2c05034
• Welsh, E. N.; Robertson, K. N.; Speed, A. W. Gram-scale synthesis of the N-phenyl phenothiazine photocatalyst by benzyne addition. Canadian Journal of Chemistry 2022, 100, 809–813. doi:10.1139/cjc-2022-0139
• Shennan, B. D. A.; Berheci, D.; Crompton, J. L.; Davidson, T. A.; Field, J. L.; Williams, B. A.; Dixon, D. J. Branching out: redox strategies towards the synthesis of acyclic α-tertiary ethers. Chemical Society reviews 2022, 51, 5878–5929. doi:10.1039/d1cs00669j
• Widness, J. K.; Enny, D. G.; McFarlane-Connelly, K. S.; Miedenbauer, M. T.; Krauss, T. D.; Weix, D. J. CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes. Journal of the American Chemical Society 2022, 144, 12229–12246. doi:10.1021/jacs.2c03235
• Rombach, D.; Wagenknecht, H.-A. Photochemical Activation of Sulfur Hexafluoride: A Tool for Fluorination and Pentafluorosulfanylation Reactions. Synthesis 2022, 54, 4883–4894. doi:10.1055/a-1877-5231
• Kodo, T.; Nagao, K.; Ohmiya, H. Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover. Nature communications 2022, 13, 2684. doi:10.1038/s41467-022-30395-4
• Zhou, J.; Mao, L.; Wu, M.-X.; Peng, Z.; Yang, Y.; Zhou, M.; Zhao, X.-L.; Shi, X.; Yang, H.-B. Extended phenothiazines: synthesis, photophysical and redox properties, and efficient photocatalytic oxidative coupling of amines. Chemical science 2022, 13, 5252–5260. doi:10.1039/d2sc01086k
• Nakagawa, M.; Matsuki, Y.; Nagao, K.; Ohmiya, H. A Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes. Journal of the American Chemical Society 2022, 144, 7953–7959. doi:10.1021/jacs.2c00527
• Wang, R.; Zhou, C.; Huang, X.; Wu, J.-Y.; Zhang, X. Phenylphenothiazine-Based Porous Organic Polymers as Visible-Light Heterogeneous Photocatalysts for Switchable Bromoalkylation and Cyclopropanation of Unactivated Terminal Alkenes. ACS Sustainable Chemistry & Engineering 2022, 10, 4650–4659. doi:10.1021/acssuschemeng.2c00054
• González-Muñoz, D.; Gómez-Avilés, A.; Molina, C.; Bedia, J.; Belver, C.; Alemán, J.; Cabrera, S. Anchoring of 10-phenylphenothiazine to mesoporous silica materials: A water compatible organic photocatalyst for the degradation of pollutants. Journal of Materials Science & Technology 2022, 103, 134–143. doi:10.1016/j.jmst.2021.07.004
• Huang, Y.-R.; Hsiao, S.-H. Electrochemical and electrochromic properties of arylene diimide dyes with N-phenylphenothiazine units. Dyes and Pigments 2022, 199, 110056. doi:10.1016/j.dyepig.2021.110056
• Wagenknecht, H.-A.; Weick, F.; Steuernagel, D.; Belov, A. Complementary Photocatalytic Toolbox: Control of Intramolecular endo- versus exo-trig Cyclizations of α-Phenyl Olefins to Oxaheterocyclic Products. Synlett 2022, 33, 1199–1204. doi:10.1055/s-0040-1719871
• Xia, W.; Zhou, Z.-A.; Lv, J.; Xiang, S.-H.; Wang, Y.-B.; Tan, B. Facile synthesis of N-aryl phenothiazines and phenoxazines via Brønsted acid catalyzed C-H amination of arenes. Chemical communications (Cambridge, England) 2022, 58, 1613–1616. doi:10.1039/d1cc06730c

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