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Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor

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References

  1. Gosmini C., Moncomble A., Isr. J. Chem., 2010, 50(5/6), 568

    Article  CAS  Google Scholar 

  2. Liegault B., Lapointe D., Caron L., Vlassova A., Fagnou K., J. Org. Chem., 2009, 74(5), 1826

    Article  CAS  PubMed  Google Scholar 

  3. Lorpaiboon W., Bovonsombat P., Org. Biomol. Chem., 2021, 19(35), 7518

    Article  CAS  PubMed  Google Scholar 

  4. Satpute D. P., Vaidya G. N., Lokhande S. K., Shinde S. D., Bhujbal S. M., Chatterjee D. R., Rana P., Venkatesh A., Nagpure M., Kumar D., Green Chem., 2021, 23(17), 6273

    Article  CAS  Google Scholar 

  5. Li L., Liu W., Mu X., Mi Z., Li C. J., Nat. Protoc., 2016, 11(10), 1948

    Article  CAS  PubMed  Google Scholar 

  6. Prier C. K., Rankic D. A., MacMillan D. W., Chem. Rev., 2013, 113(7), 5322

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Saikia I., Borah A. J., Phukan P., Chem. Rev., 2016, 116(12), 6837

    Article  CAS  PubMed  Google Scholar 

  8. Ma D. W., Xia C. F., Jiang J. Q., Zhang J. H., Org. Lett., 2001, 3(14), 2189

    Article  CAS  PubMed  Google Scholar 

  9. Ghosh S., Shashidhar J., Tetrahedron Lett., 2009, 50(11), 1177

    Article  CAS  Google Scholar 

  10. Varenikov A., Shapiro E., Gandelman M., Chem. Rev., 2021, 121(1), 412

    Article  CAS  PubMed  Google Scholar 

  11. Cresswell A. J., Eey S. T., Denmark S. E., Angew. Chem. Int. Ed., 2015, 54(52), 15642

    Article  CAS  Google Scholar 

  12. Song S., Sun X., Li X., Yuan Y., Jiao N., Org. Lett., 2015, 17(12), 2886

    Article  CAS  PubMed  Google Scholar 

  13. Rogers D. A., Brown R. G., Brandeburg Z. C., Ko E. Y., Hopkins M. D., LeBlanc G., Lamar A. A., ACS Omega, 2018, 3(10), 12868

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Kathiravan S., Nicholls I. A., Chem. Eur. J., 2017, 23(29), 7031

    Article  CAS  PubMed  Google Scholar 

  15. Romero N. A., Nicewicz D. A., Chem. Rev., 2016, 116(17), 10075

    Article  CAS  PubMed  Google Scholar 

  16. Fan J., Wei Q., Zhu E., Gao J., Cheng X., Lu Y., Loh T. P., Chem. Commun., 2021, 57(48), 5977

    Article  CAS  Google Scholar 

  17. Ohkubo K., Mizushima K., Iwata R., Fukuzumi S., Chem. Sci., 2011, 2(4), 715

    Article  CAS  Google Scholar 

  18. Petzold D., König B., Adv. Synth. Catal., 2018, 360(4), 626

    Article  CAS  Google Scholar 

  19. Ramachandran M. S., Easwaramoorthy D., Vasanthkumar S., J. Org. Chem., 1996, 61(13), 4336

    Article  CAS  PubMed  Google Scholar 

  20. Ramachandran M. S., Easwaramoorthy D., Rajasingh V., Vivekanandam T. S., Bull. Chem. Soc. Jpn., 1990, 63(8), 2397

    Article  CAS  Google Scholar 

  21. Gopalakrishnan G., Hogg J. L., J. Org. Chem., 1985, 50(8), 1206

    Article  CAS  Google Scholar 

  22. Yokoyama Y., Yamaguchi T., Sato M., Kobayashi E., Murakami Y., Okuno H., Chem. Pharm. Bull. (Tokyo), 2006, 54(12), 1715

    Article  CAS  Google Scholar 

  23. Li L., Liu W., Zeng H., Mu X., Cosa G., Mi Z., Li C. J., J. Am. Chem. Soc., 2015, 137(26), 8328

    Article  CAS  PubMed  Google Scholar 

  24. Yuan Y., Yao A., Zheng Y., Gao M., Zhou Z., Qiao J., Hu J., Ye B., Zhao J., Wen H., Lei A., iScience, 2019, 12, 293

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Song S., Li X., Wei J., Wang W., Zhang Y., Ai L., Zhu Y., Shi X., Zhang X., Jiao N., Nat. Catal., 2019, 3(2), 107

    Article  Google Scholar 

  26. Obst M., Shaikh R. S., König B., Reaction Chemistry & Engineering, 2017, 2(4), 472

    Article  CAS  Google Scholar 

  27. Houghton J. A., Lee G., Am. Ind. Hyg. Assoc. J., 1961, 22, 296

    Article  CAS  PubMed  Google Scholar 

  28. Spiesecke H., Schneider W. G., J. Chem. Phys., 1961, 35(2), 731

    Article  CAS  Google Scholar 

  29. Hansch C., Leo A., Taft R. W., Chem. Rev., 2002, 91(2), 165

    Article  Google Scholar 

  30. Sato S., Nakamura H., Angew. Chem. Int. Ed. Engl., 2013, 52(33), 8681

    Article  CAS  PubMed  Google Scholar 

  31. Alvarez Dorta D., Deniaud D., Mevel M., Gouin S. G., Chem. Eur. J., 2020, 26(63), 14257

    Article  CAS  PubMed  Google Scholar 

  32. Krygowski T. M., Dobrowolski M. A., Zborowski K., Cyrański M. K., J. Phys. Org. Chem., 2006, 19(12), 889

    Article  CAS  Google Scholar 

  33. Li L., Mu X., Liu W., Wang Y., Mi Z., Li C. J., J. Am. Chem. Soc., 2016, 138(18), 5809

    Article  CAS  PubMed  Google Scholar 

  34. Basle E., Joubert N., Pucheault M., Chem. Biol., 2010, 17(3), 213

    Article  CAS  PubMed  Google Scholar 

  35. Sakamoto S., Hamachi I., Anal. Sci., 2019, 35(1), 5

    Article  CAS  PubMed  Google Scholar 

  36. Kee C. W., Tack O., Guibbal F., Wilson T. C., Isenegger P. G., Imiolek M., Verhoog S., Tilby M., Boscutti G., Ashworth S., Chupin J., Kashani R., Poh A. W. J., Sosabowski J. K., Macholl S., Plisson C., Cornelissen B., Willis M. C., Passchier J., Davis B. G., Gouverneur V., J. Am. Chem. Soc., 2020, 142(3), 1180

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Cardinal P., Greer B., Luong H., Tyagunova Y., J. Chem. Educ., 2012, 89(8), 1061

    Article  CAS  Google Scholar 

  38. Lu L., Li Y., Jiang X., Green Chem., 2020, 22(18), 5989

    Article  CAS  Google Scholar 

  39. Cernak T., Dykstra K. D., Tyagarajan S., Vachal P., Krska S. W., Chem. Soc. Rev., 2016, 45(3), 546

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the National Key R&D Program of China(No. 2019YFE0119300), the National Natural Science Foundation of China(Nos. 32088101, 91853101), the Grant from Chinese Academy of Sciences(No.ZDBS-LY-SLH032), the Natural Science Foundation of Liaoning Province, China(No. 2019-YQ-07), the Dalian Science and Technology Innovation Foundation, China (No.2019J11CY019), and the Grant from Dalian Institute of Chemical Physics, CAS(No.DICP I202007).

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Correspondence to Fangjun Wang.

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40242_2021_1413_MOESM1_ESM.pdf

Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by using a Rotating Ultraviolet Photoreactor

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Zhang, T., Luo, P., Lai, C. et al. Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor. Chem. Res. Chin. Univ. 38, 505–509 (2022). https://doi.org/10.1007/s40242-021-1413-y

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