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Synthesis 2025; 57(22): 3481-3487
DOI: 10.1055/a-2705-4304
DOI: 10.1055/a-2705-4304
Paper
Published as part of the Special Topic Dedicated to Prof. Paul Knochel
Photoinduced Deaminative C(sp3)–H Bond diarylation of glycine derivatives by cerium catalysis
Autoren
This work was financial support from the National Natural Science Foundation of China (22171220); Fundamental Research Funds for the Central Universities (xtr072022003), and Natural Science Basic Research Plan in Shaanxi Province of China (2022JQ-130).
Abstract
A Ce(III)-catalyzed, visible light–induced aerobic oxidative diarylation of glycine derivatives with electron-rich aromatics is described. This method enables the efficient and rapid synthesis of diarylmethane derivatives under mild conditions, using air as the oxidant and obviating the need for an external photosensitizer. It is noteworthy that this protocol can be scaled up to 5 mmol without a significant impact on the efficiency.
Keywords
Glycine derivative - Visible-light induced - Photosensitizers free - Diarylation - Cerium catalysisPublikationsverlauf
Eingereicht: 10. Juli 2025
Angenommen nach Revision: 02. September 2025
Accepted Manuscript online:
19. September 2025
Artikel online veröffentlicht:
10. Oktober 2025
© 2025. Thieme. All rights reserved.
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References
- 1a Welch WM, Kraska AR, Sarges R, Koe BK. J Med Chem 1984; 27: 1508
- 1b Zara-Kaczian E, Gyorgy L, Deak G, Seregi A, Doda M. J Med Chem 1986; 29: 1189
- 1c Nilvebrant L, Andersson KE, Gillberg PG, Stahl M, SpaRf B. Eur J Pharmacol 1997; 327: 195
- 1d Hsin LW, Dersch CM, Baumann MH. et al. J Med Chem 2002; 45: 1321
- 1e Irie M. J Am Chem Soc 2002; 105: 2078
- 1f McKeage K, Keating GM. Drugs 2009; 69: 731
- 1g Malhotra B, Gandelman K, Sachse R, Wood N, Michel MC. Curr Med Chem 2009; 16: 4481
- 1h Pan P, Shen M, Yu H, Li Y, Li D, Hou T. Drug Discovery Today 2013; 18: 1323
- 1i Zhu J, Hou T, Mao X. Drug Discovery Today 2015; 20: 988
- 2a Li H, Yang J, Liu Y, Li Y. J Org Chem 2009; 74: 6797
- 2b Pratihar S. Org Biomol Chem 2016; 14: 2854
- 2c Das T, Debnath S, Maiti R, Maiti DK. J Org Chem 2017; 82: 688
- 3 Pal M, Khanal M, Marko R, Thirumalairajan S, Bearne SL. Chem Commun 2016; 52: 2740
- 4 Jadhav SD, Bakshi D, Singh A. J Org Chem 2015; 80: 10187
- 5 Song B, Himmler T, Gooßen LJ. Adv Synth Catal 2011; 353: 1688
- 6a Xi Y, Su Y, Yu Z. et al. Angew Chem Int Ed 2014; 53: 9817
- 6b Yu Z, Ma B, Chen M, Wu HH, Liu L, Zhang J. J Am Chem Soc 2014; 136: 6904
- 6c Xu B, Li ML, Zuo XD, Zhu SF, Zhou QL. J Am Chem Soc 2015; 137: 8700
- 6d Liu Y, Yu Z, Zhang JZ, Liu L, Xia F, Zhang J. Chem Sci 2016; 7: 1988
- 6e Yang JM, Cai Y, Zhu SF, Zhou QL. Org Biomol Chem 2016; 14: 5516
- 6f Yu Z, Li Y, Zhang P, Liu L, Zhang J. Chem Sci 2019; 10: 6553
- 7 Girard SA, Knauber T, Li CJ. Angew Chem Int Ed 2014; 53: 74
- 8 Ramana DV, Sudheer Kumar K, Srujana E, Chandrasekharam M. Eur J Org Chem 2019; 2019: 742
- 9 Yoo WJ, Tanoue A, Kobayashi S, Asian J. Org Chem 2014; 3: 1066
- 10a Zhang Y, Yang X, Zhou H, Li S, Zhu Y, Li Y. Org Chem Front 2018; 5: 2120
- 10b Zhu S, Rueping M. Chem Commun 2012; 48: 11960
- 11 Xu QF, Li B, Ma YJ, Sun F, Gao YN, Ye N. Org Biomol Chem 2020; 18: 666
- 12a Xuan J, Xiao WJ. Angew Chem Int Ed 2012; 51: 6828
- 12b Karkas MD, Porco Jr JA, Stephenson CR. Chem Rev 2016; 116: 9683
- 13 Prier CK, Rankic DA, MacMillan DW. Chem Rev 2013; 113: 5322
- 14 Romero NA, Nicewicz DA. Chem Rev 2016; 116: 10075
- 15a Li CJ. Acc Chem Res 2009; 42: 335
- 15b Yeung CS, Dong VM. Chem Rev 2011; 111: 1215
- 15c Liu C, Zhang H, Shi W, Lei A. Chem Rev 2011; 111: 1780
- 15d Zhang C, Tang C, Jiao N. Chem Soc Rev 2012; 41: 3464
- 15e Girard SA, Qin Y, Zhu L, Luo S. Chem Rev 2017; 117: 9433
- 16a Yoon TP, Ischay MA, Du JN. Nat Chem 2010; 2: 527
- 16b Narayanam JM, Stephenson CR. Chem Soc Rev 2011; 40: 102
- 16c Shi L, Xia W. Chem Soc Rev 2012; 41: 7687
- 17a Correa A, Segundo M. Synthesis 2018; 50: 2853
- 17b Wang C, Qi R, Wang R, Xu Z. Acc Chem Res 2023; 56: 2110
- 17c Tian Y, Bu X, Chen Y. et al. Catalysts 2023; 13: 1052
- 18a Chen L, Guo L-N, Liu S, Liu L, Duan X-H. Chem Sci 2021; 12: 1791
- 18b Xin H, Yuan Z-H, Yang M, Wang M-H, Duan X-H, Guo L-N. Green Chem 2021; 23: 9549
- 18c Yuan Z-H, Xin H, Tao J-Q, Ma Y-J, Duan X-H, Guo L-N. Org Chem Front 2022; 9: 3546
- 18d Yuan Z-H, Xin H, Zhang L. et al. Green Chem 2023; 25: 6733
- 18e Xin H, Guo L-N, Yang M, Guan C, Yuan Z-H, Duan X-H. Org Chem Front 2023; 10: 1147
- 19 Wang S, Gao Y, Hu Y. et al. Chem Commun 2023; 59: 12783
- 20 Wang S, Ye Y, Hu Y. et al. Chem Commun 2023; 59: 2628
- 21 Wang S, Ye Y, Shen H. et al. Org Biomol Chem 2023; 21: 8364
- 22a Mayr H, Lang G, Ofial AR. J Am Chem Soc 2002; 124: 4076
- 22b Huo C, Wang C, Sun C. et al. Adv Synth Catal 2013; 355: 1911
- 23 Xie J, Huang ZZ. Angew Chem Int Ed 2010; 49: 10181