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Synlett 2025; 36(02): 110-118
DOI: 10.1055/a-2312-5896
DOI: 10.1055/a-2312-5896
account
Organophotocatalytic or Electrophotocatalytic Reduction and Functionalization Reactions with a Thioxanthone-TfOH Complex Catalyst
We acknowledge the Shanghai Science and Technology Committee (21JM0010600) for financial support.
Abstract
Thioxanthone has long been a prominent catalyst in the field of photocatalysis, owing to its high triplet energy and long triplet lifetime that render it suitable for energy transfer reactions. However, its low oxidation potential and short singlet lifetime have posed challenges when employing it for electron-transfer reactions. This account summarizes our efforts in developing a potent and long-lived thioxanthone-TfOH complex (9-HTXTF) catalyst, and its application in energy-demanding redox transformations such as organophotocatalytic or electrophotocatalytic reduction and functionalization reactions.
1 Introduction
2 Discovery and Properties of the Catalyst 9-HTXTF
3 Organophotocatalysis
4 Electrophotocatalysis
5 Conclusion
Publication History
Received: 25 March 2024
Accepted after revision: 23 April 2024
Accepted Manuscript online:
23 April 2024
Article published online:
17 May 2024
© 2024. Thieme. All rights reserved
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References
- 1a Reed NL, Yoon TP. Chem. Soc. Rev. 2021; 50: 2954
- 1b Großkopf J, Kratz T, Rigotti T, Bach T. Chem. Rev. 2022; 122: 1626
- 1c Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai HA, Seath CP, MacMillan DW. C. Chem. Rev. 2022; 122: 1485
- 1d Allen AR, Noten EA, Stephenson CR. J. Chem. Rev. 2022; 122: 2695
- 1e Candish L, Collins KD, Cook GC, Douglas JJ, Gómez-Suárez A, Jolit A, Keess S. Chem. Rev. 2022; 122: 2907
- 1f de Robichon M, Kratz T, Beyer F, Zuber J, Merten C, Bach T. J. Am. Chem. Soc. 2023; 145: 24466
- 1g Yan P, Stegbauer S, Wu Q, Kolodzeiski E, Stein CJ, Lu P, Bach T. Angew. Chem. Int. Ed. 2024; 63: e202318126
- 2 Pitre SP, Overman LE. Chem. Rev. 2022; 122: 1717
- 3a Ghosh I, Ghosh T, Bardagi JI, König B. Science 2014; 346: 725
- 3b MacKenzie IA, Wang L, Onuska NP. R, Williams OF, Begam K, Moran AM, Dunietz BD, Nicewicz DA. Nature 2020; 580: 76
- 3c Glaser F, Kerzig C, Wenger OS. Angew. Chem. Int. Ed. 2020; 59: 10266
- 4 Huang H, Steiniger KA, Lambert TH. J. Am. Chem. Soc. 2022; 144: 12567
- 5 Capaldo L, Quadri LL, Ravelli D. Angew. Chem. Int. Ed. 2019; 58: 17508
- 6a Zeng L, Liu T, He C, Shi D, Zhang F, Duan C. J. Am. Chem. Soc. 2016; 138: 3958
- 6b Ghosh I, König B. Angew. Chem. Int. Ed. 2016; 55: 7676
- 6c Connell TU, Fraser CL, Czyz ML, Smith ZM, Hayne DJ, Doeven EH, Agugiaro J, Wilson DJ. D, Adcock JL, Scully AD, Gómez DE, Barnett NW, Polyzos A, Francis PS. J. Am. Chem. Soc. 2019; 141: 17646
- 6d Kerzig C, Guo X, Wenger OS. J. Am. Chem. Soc. 2019; 141: 2122
- 6e Giedyk M, Narobe R, Weiß S, Touraud D, Kunz W, König B. Nat. Catal. 2020; 3: 40
- 6f Forni JA, Micic N, Connell TU, Weragoda G, Polyzos A. Angew. Chem. Int. Ed. 2020; 59: 18646
- 6g Chmiel AF, Williams OP, Chernowsky CP, Yeung CS, Wickens ZK. J. Am. Chem. Soc. 2021; 143: 10882
- 6h Xu J, Cao J, Wu X, Wang H, Yang X, Tang X, Toh RW, Zhou R, Yeow EK. L, Wu J. J. Am. Chem. Soc. 2021; 143: 13266
- 6i Widness JK, Enny DG, McFarlane-Connelly KS, Miedenbauer MT, Krauss TD, Weix DJ. J. Am. Chem. Soc. 2022; 144: 12229
- 7 Rombach D, Wagenknecht H.-A. ChemCatChem 2018; 10: 2955
- 8a Song L, Wang W, Yue J.-P, Jiang Y.-X, Wei M.-K, Zhang H.-P, Yan S.-S, Liao L.-L, Yu D.-G. Nat. Catal. 2022; 5: 832
- 8b Chen L, Qu Q, Ran CK, Wang W, Zhang W, He Y, Liao LL, Ye JH, Yu DG. Angew. Chem. Int. Ed. 2023; 62: e202217918
- 9 Targos K, Williams OP, Wickens ZK. J. Am. Chem. Soc. 2021; 143: 4125
- 10 Cole JP, Chen D.-F, Kudisch M, Pearson RM, Lim C.-H, Miyake GM. J. Am. Chem. Soc. 2020; 142: 13573
- 11a Yan H, Hou ZW, Xu HC. Angew. Chem. Int. Ed. 2019; 58: 4592
- 11b Zhang L, Liardet L, Luo J, Ren D, Grätzel M, Hu X. Nat. Catal. 2019; 2: 366
- 11c Huang H, Strater ZM, Rauch M, Shee J, Sisto TJ, Nuckolls C, Lambert TH. Angew. Chem. Int. Ed. 2019; 58: 13318
- 11d Wang F, Stahl SS. Angew. Chem. Int. Ed. 2019; 58: 6385
- 11e Huang H, Strater ZM, Lambert TH. J. Am. Chem. Soc. 2020; 142: 1698
- 11f Xu P, Chen P.-Y, Xu H.-C. Angew. Chem. Int. Ed. 2020; 59: 14275
- 11g Lai X.-L, Shu X.-M, Song J, Xu H.-C. Angew. Chem. Int. Ed. 2020; 59: 10626
- 11h Niu L, Jiang C, Liang Y, Liu D, Bu F, Shi R, Chen H, Chowdhury AD, Lei A. J. Am. Chem. Soc. 2020; 142: 17693
- 11i Shen T, Lambert TH. J. Am. Chem. Soc. 2021; 143: 8597
- 11j Huang H, Lambert TH. Angew. Chem. Int. Ed. 2021; 60: 11163
- 11k Wu S, Žurauskas J, Domański M, Hitzfeld PS, Butera V, Scott DJ, Rehbein J, Kumar A, Thyrhaug E, Hauer J, Barham JP. Org. Chem. Front. 2021; 8: 1132
- 11l Capaldo L, Quadri LL, Merli D, Ravelli D. Chem. Commun. 2021; 57: 4424-4427
- 12a Cowper NG. W, Chernowsky CP, Williams OP, Wickens ZK. J. Am. Chem. Soc. 2020; 142: 2093
- 12b Kim H, Kim H, Lambert TH, Lin S. J. Am. Chem. Soc. 2020; 142: 2087
- 13 Zhang W, Carpenter KL, Lin S. Angew. Chem. Int. Ed. 2020; 59: 409
- 14 Shen T, Lambert TH. Science 2021; 371: 620
- 15a Huang H, Lambert TH. J. Am. Chem. Soc. 2021; 143: 7247
- 15b Huang H, Lambert TH. J. Am. Chem. Soc. 2022; 144: 18803
- 16a Tian X, Karl TA, Reiter S, Yakubov S, de Vivie-Riedle R, König B, Barham JP. Angew. Chem. Int. Ed. 2021; 60: 20817
- 16b Chernowsky CP, Chmiel AF, Wickens ZK. Angew. Chem. Int. Ed. 2021; 60: 21418
- 17 Chen Y.-J, Deng W.-H, Guo J.-D, Ci R.-N, Zhou C, Chen B, Li X.-B, Guo X.-N, Liao R.-Z, Tung C.-H, Wu L.-Z. J. Am. Chem. Soc. 2022; 144: 17261
- 18a Lai XL, Chen M, Wang Y, Song J, Xu HC. J. Am. Chem. Soc. 2022; 144: 20201
- 18b Cai C.-Y, Lai X.-L, Wang Y, Hu H.-H, Song J, Yang Y, Wang C, Xu H.-C. Nat. Catal. 2022; 5: 943
- 19 Lepori M, Schmid S, Barham JP. Beilstein J. Org. Chem. 2023; 19: 1055
- 20 Kleinmans R, Pinkert T, Dutta S, Paulisch TO, Keum H, Daniliuc CG, Glorius F. Nature 2022; 605: 477
- 21 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 22 Kang W.-J, Li B, Duan M, Pan G, Sun W, Ding A, Zhang Y, Houk KN, Guo H. Angew. Chem. Int. Ed. 2022; 61: e202211562
- 23 Kang W.-J, Li B, Zhao Z, Sun S, Feng C, Hu K, Houk KN, Guo H. ACS Catal. 2023; 13: 13588
- 24 Kang W.-J, Pan Y, Ding A, Guo H. Org. Lett. 2023; 25: 7633
- 25a Gosztola D, Niemczyk MP, Svec W, Lukas AS, Wasielewski MR. J. Phys. Chem. A 2000; 104: 6545
- 25b Beckwith JS, Aster A, Vauthey E. Phys. Chem. Chem. Phys. 2022; 24: 568
- 25c Jeong DY, Lee DS, Lee HL, Nah S, Lee JY, Cho EJ, You Y. ACS Catal. 2022; 12: 6047
- 26a Christensen JA, Phelan BT, Chaudhuri S, Acharya A, Batista VS, Wasielewski MR. J. Am. Chem. Soc. 2018; 140: 5290
- 26b Kumar A, Malevich P, Mewes L, Wu S, Barham JP, Hauer J. J. Chem. Phys. 2023; 158: 144201
- 27 Kang W.-J, Zhang Y, Li B, Guo H. Nat. Commun. 2024; 15: 655