Citation: Zhixiang Li, Zhirong Yang, Chang Yao, Bin Wu, Gang Qian, Xuezhi Duan, Xinggui Zhou, Jing Zhang. Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor[J]. Chinese Chemical Letters, ;2024, 35(4): 108893. doi: 10.1016/j.cclet.2023.108893 shu

Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor

Zhixiang Li ^{a, 1} ,
Zhirong Yang ^{b, 1} ,
Chang Yao ^a ,
Bin Wu ^a ,
Gang Qian ^a ,
Xuezhi Duan ^a ,
Xinggui Zhou ^{a, *,} ,
Jing Zhang ^{a, *,}

a.
State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China

xgzhou@ecust.edu.cn

jingzhang8507@ecust.edu.cn

Received Date: 12 May 2023
Revised Date: 31 July 2023
Accepted Date: 3 August 2023
Available Online: 6 August 2023

Figures(3)

2-Hydroxycarbazole and 4-hydroxycarbazole are important chemicals with extensive applications in optoelectronic materials and pharmaceutical field. State of the art yield of 2-hydroxycarbazole is ~30% and the reaction time is typically in hours or days. Herein, we developed a green route for the continuous and high-throughput synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole via photochemical intramolecular cyclization of 3‑hydroxy-2′‑chloro-diphenylamine using a self-designed millimeter scale photoreactor, which was designed based on sizing-up and numbering-up strategies for a decent liquid holdup (6.8 mL) and fabricated via femtosecond laser engraving technique. The photochemical synthesis was carried out continuously under the illumination of 365 nm UV-LED with dimethyl sulfoxide as solvent and potassium t-butoxide as catalyst. It was found that under optimized conditions a 2-hydroxycarbazole yield of 31.6% and a 4-hydroxycarbazole yield of 11.1% were obtained with a residence time of 1 min. Compared to semi-batch operations, the reaction time was shortened by 1–2 orders of magnitude. As a result, a throughput of 11.3 g/day 2-hydroxycarbazole and 4.0 g/day 4-hydroxycarbazole can be achieved from the photoreactor. It was proposed that the short reaction time and high product yield are resulted from higher photon transfer rates and more uniform photon distribution provided by the millimeter scale photoreactor, which enhances the reaction rates and mitigates overreaction.
- Millimeter scale reactor,
- 2-Hydroxycarbazole,
- Photochemistry,
- UV-LED,
- Process intensification
1. [1]
  M.S. Joshi, A.I. Lansakara, F.C. Pigge, Tetrahedron Lett. 56 (2015) 3204–3207. doi: 10.1016/j.tetlet.2014.12.074
2. [2]
  H.M. Kim, J.M. Choi, J.Y. Lee, Org. Electron. 43 (2017) 130–135. doi: 10.1016/j.orgel.2017.01.021
3. [3]
  S.M. Kim, J.H. Yun, S.H. Han, J.Y. Lee, J. Ind. Eng. Chem. 84 (2020) 217–225. doi: 10.1016/j.jiec.2019.12.036
4. [4]
  Y. Ou, N. Jiao, Chem. Commun. 49 (2013) 3473–3475. doi: 10.1039/c3cc41443d
5. [5]
  J.M. Thomas, G.C. Churchill, S. Patel, A. Galione, J. Pharmacol. Exp. Ther. 298 (2001) 644–650.
6. [6]
  S.C. Tovey, C.L. Longland, M. Mezna, F. Michelangeli, Eur. J. Pharmacol. 354 (1998) 245–251. doi: 10.1016/S0014-2999(98)00446-4
7. [7]
  G. Smolinsky, J. Am. Chem. Soc. 83 (1961) 2489–2493. doi: 10.1021/ja01472a016
8. [8]
  K. Lauer, E. Kiegel, DE2928483B1, 1980.
9. [9]
  A. Kawada, M. Komori, T. Nakagawa, K. Ishikawa, Patent: JP2003160516A, 2003.
10. [10]
  T.L.S. Kishbaugh, G.W. Gribble, Tetrahedron Lett. 42 (2001) 4783–4785. doi: 10.1016/S0040-4039(01)00854-1
11. [11]
  R. Sanz, J. Escribano, M.R. Pedrosa, R. Aguado, F.J. Arnaiz, Adv. Synth. Catal. 349 (2007) 713–718. doi: 10.1002/adsc.200600384
12. [12]
  O. Sonoda, T. Miyai, Patent: JP2002241365A, 2002.
13. [13]
  T. Noel, J. Flow. Chem. 7 (2017) 87–93. doi: 10.1556/1846.2017.00022
14. [14]
  F. Politano, G. Oksdath-Mansilla, Org. Process Res. Dev. 22 (2018) 1045–1062. doi: 10.1021/acs.oprd.8b00213
15. [15]
  N. Hoffmann, Chem. Rev. 108 (2008) 1052–1103. doi: 10.1021/cr0680336
16. [16]
  X. Shi, S. Liu, C. Duanmu, et al., Chem. Eng. J. 420 (2021) 129976. doi: 10.1016/j.cej.2021.129976
17. [17]
  C. Shen, M. Shang, H. Zhang, Y. Su, AlChE J. 66 (2020) e16841. doi: 10.1002/aic.16841
18. [18]
  Y. Wang, C. Shen, M. Qiu, M. Shang, Y. Su, AlChE J. 69 (2023) e18102. doi: 10.1002/aic.18102
19. [19]
  T. Aillet, K. Loubiere, O. Dechy-Cabaret, L. Prat, Int. J. Chem. React. Eng. 12 (2014) 257–269. doi: 10.1515/ijcre-2013-0121
20. [20]
  S. Bachollet, K. Terao, S. Aida, et al., Beilstein J. Org. Chem. 9 (2013) 2015–2021. doi: 10.3762/bjoc.9.237
21. [21]
  M. Conradi, T. Junkers, J. Photochem. Photobiol. A 259 (2013) 41–46. doi: 10.1016/j.jphotochem.2013.02.024
22. [22]
  T. Fukuyama, Y. Kajihara, Y. Hino, I. Ryu, J. Flow. Chem. 1 (2011) 40–45.
23. [23]
  A. Talla, B. Driessen, N.J.W. Straathof, et al., Adv. Synth. Catal. 357 (2015) 2180–2186. doi: 10.1002/adsc.201401010
24. [24]
  K. Donnelly, M. Baumann, J. Flow. Chem. 11 (2021) 223–241. doi: 10.1007/s41981-021-00168-z
25. [25]
  T. Fukuyama, T. Kasakado, M. Hyodo, I. Ryu, Photochem. Photobiol. Sci. 21 (2022) 761–775. doi: 10.1007/s43630-021-00151-6
26. [26]
  K.P.L. Kuijpers, M.A.H. van Dijk, Q.G. Rumeur, et al., React. Chem. Eng. 2 (2017) 109–115. doi: 10.1039/C7RE00024C
27. [27]
  Y. Su, N.J.W. Straathof, V. Hessel, T. Noel, Chem. Eur. J. 20 (2014) 10562–10589. doi: 10.1002/chem.201400283
28. [28]
  D. Cambié, C. Bottecchia, N.J.W. Straathof, V. Hessel, T. Noël, Chem. Rev. 116 (2016) 10276–10341. doi: 10.1021/acs.chemrev.5b00707
29. [29]
  L. Buglioni, F. Raymenants, A. Slattery, S.D. Zondag, T. Noël, Chem. Rev. 122 (2021) 2752–2906.
30. [30]
  T. Noël, Photochemical Processes in Continuous-Flow Reactors, 1st ed., World Scientific, 2017.
31. [31]
  H. Lv, Z. Yang, J. Zhang, et al., Micromachines 12 (2021) 883. doi: 10.3390/mi12080883
32. [32]
  H. Lv, J. Wang, Z. Shu, et al., Chin. Chem. Lett. 34 (2023) 107710. doi: 10.1016/j.cclet.2022.07.053
33. [33]
  M.E. Budén, V.A. Vaillard, S.E. Martin, R.A. Rossi, J. Org. Chem. 74 (2009) 4490–4498. doi: 10.1021/jo9006249
34. [34]
  A. Albini, M. Fagnoni, Handbook of Synthetic Photochemistry, 1st ed., Wiley, 2009.
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