Sulfonyl fluoride synthesis via visible-light-mediated fluorosulfonylation of thianthrenium salts

References

• Dong, J.; Krasnova, L.; Finn, M. G.; Sharpless, K. B. Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry. Angew. Chem. Int. Ed. Engl. 2014, 53, 9430–9448. DOI: 10.1002/anie.201309399.
   PubMed Web of Science ®Google Scholar
• Xu, L.; Dong, J. Click Chemistry: Evolving on the Fringe. Chin. J. Chem. 2020, 38, 414–419. DOI: 10.1002/cjoc.201900421.
   Web of Science ®Google Scholar
• Jones, L. H. Emerging Utility of Fluorosulfate Chemical Probes. ACS Med. Chem. Lett. 2018, 9, 584–586. DOI: 10.1021/acsmedchemlett.8b00276.
   PubMed Web of Science ®Google Scholar
• Liu, Z.; Li, J.; Li, S.; Li, G.; Sharpless, K. B.; Wu, P. SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization. J. Am. Chem. Soc. 2018, 140, 2919–2925. DOI: 10.1021/jacs.7b12788.
   PubMed Web of Science ®Google Scholar
• Barrow, A.; Smedley, C. J.; Zheng, Q.; Li, S.; Dong, J.; Moses, J. E. The Growing Applications of SuFEx Click Chemistry. Chem. Soc. Rev. 2019, 48, 4731–4758. DOI: 10.1039/C8CS00960K.
   PubMed Web of Science ®Google Scholar
• Lee, C.; Cook, A.; Elisabeth, J. E.; Friede, N. C.; Sammis, G. M.; Ball, N. D. The Emerging Applications of Sulfur(VI) Fluorides in Catalysis. ACS Catal. 2021, 11, 6578–6589. DOI: 10.1021/acscatal.1c01201.
   PubMed Web of Science ®Google Scholar
• Carneiro, S. N.; Khasnavis, S. R.; Lee, J.; Butler, T. W.; Majmudar, J. D.; Ende, C. W. A.; Ball, N. D. Sulfur(VI) Fluorides as Tools in Biomolecular and Medicinal Chemistry, Org. Biomol. Chem. 2023, 21, 1356–1372. DOI: 10.1039/D2OB01891H.
   PubMed Web of Science ®Google Scholar
• Lekkala, R.; Lekkala, R.; Moku, B.; Rakesh, K. P.; Qin, H. Applications of Sulfuryl Fluoride (SO2F2) in Chemical Transformations. Org. Chem. Front. 2019, 6, 3490–3516. DOI: 10.1039/C9QO00747D.
   Web of Science ®Google Scholar
• Meng, Y.; Wang, S.; Fang, W.; Xie, Z.; Leng, J.; Alsulami, H.; Qin, H. Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More. Synthesis. 2020, 52, 673–687. DOI: 10.1055/s-0039-1690038.
   Web of Science ®Google Scholar
• Zhong, T.; Chen, Z.; Yi, J.; Lu, G.; Weng, J. Recent Progress in the Synthesis of Sulfonyl Fluorides for SuFEx Click Chemistry. Chin. Chem. Lett. 2021, 32, 2736–2750. DOI: 10.1016/j.cclet.2021.03.035.
   Web of Science ®Google Scholar
• Chelagha, A.; Louvel, D.; Taponard, A.; Berthelon, R.; Tlili, A. Synthetic Routes to Arylsulfonyl Fluorides. Catalysts. 2021, 11, 830. DOI: 10.3390/catal11070830.
   Web of Science ®Google Scholar
• He, F.-S.; Li, Y.-Q.; Wu, J. Fluorosulfonyl Radicals: New Horizons for the Synthesis of Sulfonyl Fluorides. Org. Chem. Front. 2022, 9, 5299–5305. DOI: 10.1039/D2QO01211A.
   Web of Science ®Google Scholar
• Lou, T. S. B.; Willis, M. C. Sulfonyl Fluorides as Targets and Substrates in the Development of New Synthetic Methods. Nat. Rev. Chem. 2022, 6, 146–162. DOI: 10.1038/s41570-021-00352-8.
   PubMed Web of Science ®Google Scholar
• Barata-Vallejo, S.; Yerien, D. E.; Postigo, A. Synthetic Strategies for Fluorosulfonylated Compounds: Application to Click Chemistry Reactions. Catal. Sci. Technol. 2023, 13, 2597–2617. DOI: 10.1039/D2CY01998A.
   Web of Science ®Google Scholar
• Laudadio, G.; Bartolomeu, A. A.; Verwijlen, L. M. H. M.; Cao, Y.; Oliveira, K. T.; Noël, T. Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride. J. Am. Chem. Soc. 2019, 141, 11832–11836. DOI: 10.1021/jacs.9b06126.
   PubMed Web of Science ®Google Scholar
• Wright, S. W.; Hallstrom, K. N. A Convenient Preparation of Heteroaryl Sulfonamides and Sulfonyl Fluorides from Heteroaryl Thiols. J. Org. Chem. 2006, 71, 1080–1084. DOI: 10.1021/jo052164+.
   PubMed Web of Science ®Google Scholar
• Jiang, Y.; Alharbi, N. S.; Sun, B.; Qin, H.-L. Facile One-Pot Synthesis of Sulfonyl Fluorides from Sulfonates or Sulfonic Acids. RSC Adv. 2019, 9, 13863–13867. DOI: 10.1039/C9RA02531F.
   PubMed Web of Science ®Google Scholar
• Thomson, B. J.; Khasnavis, S. R.; Grigorian, E. C.; Krishnan, R.; Yassa, T. D.; Lee, K.; Sammis, G. M.; Ball, N. D. Facile Synthesis of Sulfonyl Fluorides from Sulfonic Acids. Chem. Commun. 2023, 59, 555–558. DOI: 10.1039/D2CC05781F.
   PubMed Web of Science ®Google Scholar
• Tang, L.; Yang, Y.; Wen, L.; Yang, X.; Wang, Z. Catalyst-Free Radical Fluorination of Sulfonyl Hydrazides in Water. Green Chem. 2016, 18, 1224–1228. DOI: 10.1039/C5GC02755A.
   Web of Science ®Google Scholar
• Toulgoat, F.; Langlois, B. R.; Médebielle, M.; Sanchez, J.-Y. An Efficient Preparation of New Sulfonyl Fluorides and Lithium Sulfonates. J. Org. Chem. 2007, 72, 9046–9052. DOI: 10.1021/jo701318n.
   PubMed Web of Science ®Google Scholar
• Zhang, L.; Cheng, X.; Zhou, Q.-L. Electrochemical Synthesis of Sulfonyl Fluorides with Triethylamine Hydrofluoride. Chin. J. Chem. 2022, 40, 1687–1692. DOI: 10.1002/cjoc.202200112.
   Web of Science ®Google Scholar
• Davies, A. T.; Curto, J. M.; Bagley, S. W.; Willis, M. C. One-Pot Palladium-Catalyzed Synthesis of Sulfonyl Fluorides from Aryl Bromides. Chem. Sci. 2017, 8, 1233–1237. DOI: 10.1039/C6SC03924C.
   PubMed Web of Science ®Google Scholar
• Tribby, A. L.; Rodríguez, I.; Shariffudin, S.; Ball, N. D. Pd-Catalyzed Conversion of Aryl Iodides to Sulfonyl Fluorides Using SO2 Surrogate DABSO and Selectfluor. J. Org. Chem. 2017, 82, 2294–2299. DOI: 10.1021/acs.joc.7b00051.
   PubMed Web of Science ®Google Scholar
• Shavnya, A.; Coffey, S. B.; Hesp, K. D.; Ross, S. C.; Tsai, A. S. Reaction of Alkyl Halides with Rongalite: One-Pot and Telescoped Synthesis of Aliphatic Sulfonamides, Sulfonyl Fluorides and Unsymmetrical Sulfones. Org. Lett. 2016, 18, 5848–5851. DOI: 10.1021/acs.orglett.6b02894.
   PubMed Web of Science ®Google Scholar
• Shavnya, A.; Hesp, K. D.; Tsai, A. S. A Versatile Reagent and Method for Direct Aliphatic Sulfonylation. Adv. Synth. Catal. 2018, 360, 1768–1774. DOI: 10.1002/adsc.201800071.
   Web of Science ®Google Scholar
• Lee, C.; Ball, N. D.; Sammis, G. M. One-Pot Fluorosulfurylation of Grignard Reagents Using Sulfuryl Fluoride. Chem. Commun. 2019, 55, 14753–14756. DOI: 10.1039/C9CC08487H.
   PubMed Web of Science ®Google Scholar
• Kwon, J.; Kim, B. M. Synthesis of Arenesulfonyl Fluorides via Sulfuryl Fluoride Incorporation from Arynes. Org. Lett. 2019, 21, 428–433. DOI: 10.1021/acs.orglett.8b03610.
   PubMed Web of Science ®Google Scholar
• Guo, T.; Meng, G.; Zhan, X.; Yang, Q.; Ma, T.; Xu, L.; Sharpless, K. B.; Dong, J. A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F-SO2+” Donor of Unprecedented Reactivity, Selectivity, and Scope. Angew. Chem. Int. Ed. Engl. 2018, 57, 2605–2610. DOI: 10.1002/anie.201712429.
   PubMed Web of Science ®Google Scholar
• Zhou, H.; Mukherjee, P.; Liu, R.; Evrard, E.; Wang, D.; Humphrey, J. M.; Butler, T. W.; Hoth, L. R.; Sperry, J. B.; Sakata, S. K.; et al. Introduction of a Crystalline, Shelfstable Reagent for the Synthesis of Sulfur (VI) Fluorides. Org. Lett. 2018, 20, 812–815. DOI: 10.1021/acs.orglett.7b03950.
   PubMed Web of Science ®Google Scholar
• Xu, R.; Xu, T.; Yang, M.; Cao, T.; Liao, S. A Rapid Access to Aliphatic Sulfonyl Fluorides. Nat. Commun. 2019, 10, 3752. DOI: 10.1038/s41467-019-11805-6.
   PubMed Web of Science ®Google Scholar
• Nie, X.; Xu, T.; Song, J.; Devaraj, A.; Zhang, B.; Chen, Y.; Liao, S. Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes. Angew. Chem. Int. Ed. Engl. 2021, 60, 3956–3960. DOI: 10.1002/anie.202012229.
   PubMed Web of Science ®Google Scholar
• Nie, X.; Xu, T.; Hong, Y.; Zhang, H.; Mao, C.; Liao, S. Introducing a New Class of Sulfonyl Fluoride Hubs via Radical Chloro-Fluorosulfonylation of Alkynes. Angew. Chem. Int. Ed. Engl. 2021, 60, 22035–22042. DOI: 10.1002/anie.202109072.
   PubMed Web of Science ®Google Scholar
• Chen, D.; Nie, X.; Feng, Q.; Zhang, Y.; Wang, Y.; Wang, Q.; Huang, L.; Huang, S.; Liao, S. Electrochemical Oxo-Fluorosulfonylation of Alkynes under Air: Facile Access to β-Keto Sulfonyl Fluorides. Angew. Chem. Int. Ed. Engl. 2021, 60, 27271–27276. DOI: 10.1002/anie.202112118.
   PubMed Web of Science ®Google Scholar
• Wang, P.; Zhang, H.; Zhao, M.; Ji, S.; Lin, L.; Yang, N.; Nie, X.; Song, J.; Liao, S. Radical Hydro-Fluorosulfonylation of Unactivated Alkenes and Alkynes. Angew. Chem. Int. Ed. 2022, 61, e202207684. DOI: 10.1002/anie.202207684.
   PubMed Web of Science ®Google Scholar
• Nie, X.; Liao, S. Radical Fluorosulfonylation: Accessing Alkenylsulfonyl Fluorides from Alkenes and Alkynes. Synlett. 2022, 33, 401–408. DOI: 10.1055/a-1700-6453.
   Web of Science ®Google Scholar
• Wang, P.; Zhang, H.; Nie, X.; Xu, T.; Liao, S. Photoredox Catalytic Radical Fluorosulfonylation of Olefins Enabled by a Bench-Stable Redox-Active Fluorosulfonyl Radical Precursor. Nat. Commun. 2022, 13, 3370. DOI: 10.1038/s41467-022-31089-7.
   PubMed Web of Science ®Google Scholar
• Feng, Q.; Fu, Y.; Zheng, Y.; Liao, S.; Huang, S. Electrochemical Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Triflates. Org. Lett. 2022, 24, 3702–3706. DOI: 10.1021/acs.orglett.2c01336.
   PubMed Web of Science ®Google Scholar
• Zhang, H.; Yang, N.; Li, J.; Wang, P.; Li, S.; Xie, L.; Liao, S. Radical Fluorosulfonyl Arylation of Alkenes: Accessing FSO2-Functionalized Chromanes via Formal Endo and Exo Cyclization. Org. Lett. 2022, 24, 8170–8175. DOI: 10.1021/acs.orglett.2c03224.
   PubMed Web of Science ®Google Scholar
• Wang, P.; Li, S.-J.; Zhang, H.; Yang, N.; Liao, S. Photo-Organocatalytic Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Acetates. Synlett. 2023, 34, 471–476. DOI: 10.1055/s-0041-1738692.
   Web of Science ®Google Scholar
• Zhang, W.; Li, H.; Li, X.; Zou, Z.; Huang, M.; Liu, J.; Wang, X.; Ni, S.; Pan, Y.; Wang, Y. A Practical Fluorosulfonylating Platform via Photocatalytic Imidazolium-Based SO2F Radical Reagent. Nat. Commun. 2022, 13, 3515. DOI: 10.1038/s41467-022-31296-2.
   PubMed Web of Science ®Google Scholar
• Liu, Y.; Wu, H.; Guo, Y.; Xiao, J.-C.; Chen, Q.-Y.; Liu, C. Trifluoromethylfluorosulfonylation of Unactivated Alkenes Using Readily Available Ag(O2CCF2SO2F) and N-Fluorobenzenesulfonimide. Angew. Chem. Int. Ed. Engl. 2017, 56, 15432–15435. DOI: 10.1002/anie.201709663.
   PubMed Web of Science ®Google Scholar
• Liu, Y.; Lin, Q.; Xiao, Z.; Zheng, C.; Guo, Y.; Chen, Q.-Y.; Liu, C. Zinc-Mediated Intermolecular Reductive Radical Fluoroalkylsulfination of Unsaturated Carbon-Carbon Bonds with Fluoroalkyl Bromides and Sulfur Dioxide. Chemistry. 2019, 25, 1824–1828. DOI: 10.1002/chem.201805526.
   PubMed Web of Science ®Google Scholar
• Lin, Q.; Liu, Y.; Xiao, Z.; Zheng, L.; Zhou, X.; Guo, Y.; Chen, Q.-Y.; Zheng, C.; Liu, C. Intermolecular Oxidative Radical Fluoroalkylfluorosulfonylation of Unactivated Alkenes with (Fluoroalkyl)Trimethylsilane, Silver Fluoride, Sulfur Dioxide and N-Fluorobenzenesulfonimide. Org. Chem. Front. 2019, 6, 447–450. DOI: 10.1039/C8QO01192C.
   Web of Science ®Google Scholar
• Liu, Y.; Yu, D.; Guo, Y.; Xiao, J.-C.; Chen, Q.-Y.; Liu, C. Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts. Org. Lett. 2020, 22, 2281–2286. DOI: 10.1021/acs.orglett.0c00484.
   PubMed Web of Science ®Google Scholar
• Lin, Q.; Ma, Z.; Zheng, C.; Hu, X.-J.; Guo, Y.; Chen, Q.-Y.; Liu, C. Arenesulfonyl Fluoride Synthesis via Copper-Free Sandmeyer-Type Fluorosulfonylation of Arenediazonium Salts. Chin. J. Chem. 2020, 38, 1107–1110. DOI: 10.1002/cjoc.202000175.
   Web of Science ®Google Scholar
• Liu, Y.; Pan, Q.; Hu, X.; Guo, Y.; Chen, Q.-Y.; Liu, C. Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides. Org. Lett. 2021, 23, 3975–3980. DOI: 10.1021/acs.orglett.1c01118.
   PubMed Web of Science ®Google Scholar
• Pan, Q.; Liu, Y.; Pang, W.; Wu, J.; Ma, X.; Hu, X.; Guo, Y.; Chen, Q.-Y.; Liu, C. Copper-Catalyzed Three-Component Reaction of Arylhydrazine Hydrochloride, DABSO, and NFSI for the Synthesis of Arenesulfonyl Fluorides. Org. Biomol. Chem. 2021, 19, 8999–9003. DOI: 10.1039/D1OB01697K.
   PubMed Web of Science ®Google Scholar
• Ma, Z.; Shan, L.; Ma, X.; Hu, X.; Guo, Y.; Chen, Q.-Y.; Liu, C. Arenesulfonyl Fluoride Synthesis via One-Pot Copper-Free Sandmeyer-Type Three-Component Reaction of Aryl Amine, K2S2O5, and NFSI. J. Fluorine Chem. 2022, 254, 109948. DOI: 10.1016/j.jfluchem.2022.109948.
   Web of Science ®Google Scholar
• Ma, Z.; Liu, Y.; Ma, X.; Hu, X.; Guo, Y.; Chen, Q.-Y.; Liu, C. Aliphatic Sulfonyl Fluoride Synthesis via Reductive Decarboxylative Fluorosulfonylation of Aliphatic Carboxylic Acid NHPI Esters. Org. Chem. Front. 2022, 9, 1115–1120. DOI: 10.1039/D1QO01655E.
   Web of Science ®Google Scholar
• Shan, L.; Ma, Z.; Ou, C.; Cai, Y.; Ma, Y.; Guo, Y.; Ma, X.; Liu, C. Aryl Sulfonyl Fluoride Synthesis via Palladium-Catalyzed Fluorosulfonylation of Aryl Thianthrenium Salts. Org. Biomol. Chem. 2023, 21, 3789–3793. DOI: 10.1039/D3OB00462G.
   PubMed Web of Science ®Google Scholar
• Zhong, T.; Pang, M.-K.; Chen, Z.-D.; Zhang, B.; Weng, J.; Lu, G. Copper-Free Sandmeyer-Type Reaction for the Synthesis of Sulfonyl Fluorides. Org. Lett. 2020, 22, 3072–3078. DOI: 10.1021/acs.orglett.0c00823.
   PubMed Web of Science ®Google Scholar
• Liu, S.; Huang, Y.; Xu, X.-H.; Qing, F.-L. Fluorosulfonylation of Arenediazonium Tetrafluoroborates with Na2S2O5 and N-Fluorobenzenesulfonimide. J. Fluorine Chem. 2020, 240, 109653. DOI: 10.1016/j.jfluchem.2020.109653.
   Web of Science ®Google Scholar
• Louvel, D.; Chelagha, A.; Rouillon, J.; Payard, P.-A.; Khrouz, L.; Monnereau, C.; Tlili, A. Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism. Chemistry. 2021, 27, 8704–8708. DOI: 10.1002/chem.202101056.
   PubMed Web of Science ®Google Scholar
• Chen, Z.-D.; Zhou, X.; Yi, J.-T.; Diao, H.-J.; Chen, Q.-L.; Lu, G.; Weng, J. Catalytic Decarboxylative Fluorosulfonylation Enabled by Energy-Transfer-Mediated Photocatalysis. Org. Lett. 2022, 24, 2474–2478. DOI: 10.1021/acs.orglett.2c00459.
   PubMed Web of Science ®Google Scholar
• Nguyen, V. T.; Haug, G. C.; Nguyen, V. D.; Vuong, N. T. H.; Karki, G. B.; Arman, H. D.; Larionov, O. V. Functional Group Divergence and the Structural Basis of Acridine Photocatalysis Revealed by Direct Decarboxysulfonylation. Chem. Sci. 2022, 13, 4170–4179. DOI: 10.1039/D2SC00789D.
   PubMed Web of Science ®Google Scholar
• Xu, T.; Cao, T.; Yang, M.; Xu, R.; Nie, X.; Liao, S. Decarboxylative Thiolation of Redox-Active Esters to Thioesters by Merging Photoredox and Copper Catalysis. Org. Lett. 2020, 22, 3692–3696. DOI: 10.1021/acs.orglett.0c01180.
   PubMed Web of Science ®Google Scholar
• Zhang, H.; Li, S.; Zheng, H.-L.; Zhu, G.; Liao, S.; Nie, X. Photocatalytic Fluorosulfonylation of Aliphatic Carboxylic Acid NHPI Esters. Org. Chem. Front. 2022, 9, 4854–4860. DOI: 10.1039/D2QO00861K.
   Web of Science ®Google Scholar
• Yi, J.-T.; Zhou, X.; Chen, Q.-L.; Chen, Z.-D.; Lu, G.; Weng, J. Copper-Catalyzed Direct Decarboxylative Fluorosulfonylation of Aliphatic Carboxylic Acids. Chem. Commun. 2022, 58, 9409–9412. DOI: 10.1039/d2cc03221j.
   PubMed Web of Science ®Google Scholar
• Sarver, P. J.; Bissonnette, N. B.; MacMillan, D. W. C. Decatungstate-Catalyzed C(sp3)−H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality. J. Am. Chem. Soc. 2021, 143, 9737–9743. DOI: 10.1021/jacs.1c04722.
   PubMed Web of Science ®Google Scholar
• Vincent, C. A.; Chiriac, M. I.; Troian-Gautier, L.; Tambar, U. K. Photocatalytic Sulfonyl Fluorination of Alkyl Organoboron Substrates. ACS Catal. 2023, 13, 3668–3675. DOI: 10.1021/acscatal.3c00107.
   PubMed Web of Science ®Google Scholar
• Zhong, T.; Yi, J. T.; Chen, Z. D.; Zhuang, Q. C.; Li, Y. Z.; Lu, G.; Weng, J. Photoredox-Catalyzed Aminofluorosulfonylation of Unactivated Olefins. Chem. Sci. 2021, 12, 9359–9365. DOI: 10.1039/D1SC02503A.
   PubMed Web of Science ®Google Scholar
• Chen, X.-Y.; Wu, Y.; Wang, P. Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes. Synthesis 2022, 54, 3928–3940. DOI: 10.1055/s-0041-1737493.
   Web of Science ®Google Scholar
• Berger, F.; Plutschack, M. B.; Riegger, J.; Yu, W.; Speicher, S.; Ho, M.; Frank, N.; Ritter, T. Site-Selective and Versatile Aromatic C-H Functionalization by Thianthrenation. Nature. 2019, 567, 223–228. DOI: 10.1038/s41586-019-0982-0.
   PubMed Web of Science ®Google Scholar
• Ye, F.; Berger, F.; Jia, H.; Ford, J.; Wortman, A.; Börgel, J.; Genicot, C.; Ritter, T. Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation, Angew. Angew. Chem. Int. Ed. Engl. 2019, 58, 14615–14619. DOI: 10.1002/anie.201906672.
   PubMed Web of Science ®Google Scholar
• Sang, R.; Korkis, S. E.; Su, W.; Ye, F.; Engl, P. S.; Berger, F.; Ritter, T. Site-Selective C-H Oxygenation via Aryl Sulfonium Salts. Angew. Chem. Int. Ed. Engl. 2019, 58, 16161–16166. DOI: 10.1002/anie.201908718.
   PubMed Web of Science ®Google Scholar
• Engl, P. S.; Häring, A. P.; Berger, F.; Berger, G.; Pérez-Bitrián, A.; Ritter, T. C-N Cross-Couplings for Site-Selective Late-Stage Diversification via Aryl Sulfonium Salts. J. Am. Chem. Soc. 2019, 141, 13346–13351. DOI: 10.1021/jacs.9b07323.
   PubMed Web of Science ®Google Scholar
• Li, J.; Chen, J.; Sang, R.; Ham, W.-S.; Plutschack, M. B.; Berger, F.; Chabbra, S.; Schnegg, A.; Genicot, C.; Ritter, T. Photoredox Catalysis with Aryl Sulfonium Salts Enables Site-Selective Late-Stage Fluorination. Nat. Chem. 2020, 12, 56–62.     DOI: 10.1038/s41557-019-0353-3.
   PubMed Web of Science ®Google Scholar
• Alvarez, E. M.; Karl, T.; Berger, F.; Torkowski, L.; Ritter, T. Late-Stage Heteroarylation of Hetero(Aryl)Sulfonium Salts Activated by α-Amino Alkyl Radicals. Angew. Chem. Int. Ed. Engl. 2021, 60, 13609–13613. DOI: 10.1002/anie.202103085.
   PubMed Web of Science ®Google Scholar
• He, F.-S.; Bao, P.; Tang, Z.; Yu, F.; Deng, W.; Wu, J. Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts. Org. Lett. 2022, 24, 2955–2960. DOI: 10.1021/acs.orglett.2c01132.
   PubMed Web of Science ®Google Scholar
• Li, Q.; Huang, J.; Cao, Z.; Zhang, J.; Wu, J. Photoredox-Catalyzed Reaction of Thianthrenium Salts, Sulfur Dioxide and Hydrazines. Org. Chem. Front. 2022, 9, 3781–3785. DOI: 10.1039/D2QO00768A.
   Web of Science ®Google Scholar
• Tang, S.; Zhao, X.; Yang, L.; Li, B.; Wang, B. Copper-Catalyzed Carboxylation of Aryl Thianthrenium Salts with CO2. Angew. Chem. Int. Ed. Engl. 2022, 61, e202212975. DOI: 10.1002/anie.202212975.
   PubMed Web of Science ®Google Scholar
• Li, X.; Si, W.; Liu, Z.; Qian, H.; Wang, T.; Leng, S.; Sun, J.; Jiao, Y.; Zhang, X. Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins. Org. Lett. 2022, 24, 4070–4074. DOI: 10.1021/acs.orglett.2c01525.
   PubMed Web of Science ®Google Scholar
• Cabrera-Afonso, M. J.; Granados, A.; Molander, G. A. Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts. Angew. Chem. Int. Ed. Engl. 2022, 61, e202202706. DOI: 10.1002/anie.202202706.
   PubMed Web of Science ®Google Scholar
• Ye, Y.; Zhu, J.; Xie, H.; Huang, Y. Rhodium-Catalyzed Divergent Arylation of Alkenylsulfonium Salts with Arylboroxines. Angew. Chem. Int. Ed. Engl. 2022, 61, e202212522. DOI: 10.1002/anie.202212522.
   PubMed Web of Science ®Google Scholar
• Ma, H.; Li, Y.; Wang, P.; Ye, J.; Zhang, J.; Liu, G.; Wu, J. Photoredox-Catalyzed Intermolecular Azidosulfonylation of Alkenes with DABCO·(SO2)2, Trimethylsilyl Azide and Thianthrenium Salts. Org. Chem. Front. 2023, 10, 866–871. DOI: 10.1039/D2QO01706G.
   Web of Science ®Google Scholar
• During the preparation of this manuscript, Kong, Cao andco-workers reported the electrochemically driven synthesisof aryl sulfonyl fluorides from thianthrenium salts, see: Kong, X.; Chen, Y.; Liu, Q.; Wang, W.; Zhang, S.; Zhang, Q.; Chen, X.; Xu, Y.-Q.; Cao, Z.-Y, Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry. Org. Lett. 2023, 25, 581–586. DOI: 10.1021/acs.orglett.2c03956.
   PubMed Web of Science ®Google Scholar
• Chao, P.; Gu, R.; Ma, X.; Wang, T.; Zhao, Y. Thiophene-Substituted Phenothiazine-Based Photosensitisers for Radical and Cationic Photopolymerization Reactions under Visible Laser Beams (405 and 455 nm). Polym. Chem. 2016, 7, 5147–5156. DOI: 10.1039/C6PY01095D.
   Web of Science ®Google Scholar