Citation: Xianjin Zhu, Yong Liu, Lunyu Ou, Haijun Yang, Hua Fu. Photocatalytic direct oxygen-isotopic labelings of carbonyls in ketones and aldehydes with oxygen-isotopic waters[J]. Chinese Chemical Letters, ;2023, 34(11): 108454. doi: 10.1016/j.cclet.2023.108454 shu

Photocatalytic direct oxygen-isotopic labelings of carbonyls in ketones and aldehydes with oxygen-isotopic waters

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

fuhua@mail.tsinghua.edu.cn

Received Date: 5 February 2023
Revised Date: 3 April 2023
Accepted Date: 12 April 2023
Available Online: 14 April 2023

Figures(6)

Oxygen-isotopic labelings play important roles in identifying and understanding chemical and biological processes. Direct C=O to C=¹⁸O or C=¹⁷O conversion in a single step leading to labeled compounds can alleviate synthetic burdens without the need for resynthesis. Here we describe a photocatalytic oxygen-isotopic labeling protocol that can efficiently and selectively install ¹⁸O and ¹⁷O on carbonyls of ketones and aldehydes via oxygen isotope exchange with oxygen-isotopic waters (H₂¹⁸O or H₂¹⁷O) as the sources of oxygen isotopes, in which light and oxygen-enabled sodium alkanesulfinates catalyzed this process. This strategy was extended to the in-situ formed ketones from the photocatalytic aerobic oxidation of alkyl arenes and secondary alcohols. Furthermore, reduction of the oxygen-isotopically labeled aldehydes with NaBH₄ provided the corresponding oxygen-isotopically labeled primary alcohols. We believe that the oxygen-isotopically labeling method will be widely used in chemistry, biology and medicine fields.
- Oxygen-isotopic labeling,
- Photocatalysis,
- Oxygen-isotopic waters,
- Compounds containing carbonyls,
- Alkanesulfinates
1. [1]
  T.G. Gant, J. Med. Chem. 57 (2014) 3595–3611. doi: 10.1021/jm4007998
2. [2]
  M. Dean, V.W. Sung, Drug Des. Devel. Ther. 12 (2018) 313–319. doi: 10.2147/DDDT.S138828
3. [3]
  P.H. Marathe, W.C. Shyu, W.G. Humphreys, Curr. Pharm. Des. 10 (2004) 2991–3008. doi: 10.2174/1381612043383494
4. [4]
  N.A. Meanwell, J. Med. Chem. 54 (2011) 2529–2591. doi: 10.1021/jm1013693
5. [5]
  S.D. Nelson, W.F. Trager, Drug Metab. Dispos. 31 (2003) 1481–1497. doi: 10.1124/dmd.31.12.1481
6. [6]
  Y.Y. Loh, K. Nagao, A.J. Hoover, et al., Science 358 (2017) 1182–1187. doi: 10.1126/science.aap9674
7. [7]
  R.P. Yu, D. Hesk, N. Rivera, I. Pelczer, P.J. Chirik, Nature 529 (2016) 195–199. doi: 10.1038/nature16464
8. [8]
  J. Atzrodt, V. Derdau, W.J. Kerr, M. Reid, Angew. Chem. Int. Ed. 57 (2018) 1758–1784. doi: 10.1002/anie.201704146
9. [9]
  C.J. Unkefera, R.A. Martinez, Drug Test Anal. 4 (2012) 303–307. doi: 10.1002/dta.361
10. [10]
  C. Zhu, F. Chen, C. Liu, et al., J. Org. Chem. 83 (2018) 14713–14722. doi: 10.1021/acs.joc.8b02103
11. [11]
  Y. Jin, L. Ou, H. Yang, H. Fu, J. Am. Chem. Soc. 139 (2017) 14237–14243. doi: 10.1021/jacs.7b07883
12. [12]
  C.N. Cornell, M.S. Sigman, J. Am. Chem. Soc. 127 (2005) 2796–2797. doi: 10.1021/ja043203m
13. [13]
  Y.W. Liu, Z.Y. Mao, X.D. Nie, et al., J. Org. Chem. 84 (2019) 16254–16261. doi: 10.1021/acs.joc.9b02854
14. [14]
  Y. Wang, X. Cao, J. Ji, et al., Chin. Chem. Lett. 32 (2021) 1696–1700. doi: 10.1016/j.cclet.2020.12.026
15. [15]
  B.H. Zhu, Y.X. Zheng, W. Kang, et al., Sci. China Chem. 64 (2021) 1985–1989. doi: 10.1007/s11426-021-1069-7
16. [16]
  M. Zheng, J. Zeng, M. Meihemuti, A.R. Abulikemu. Chin. J. Org. Chem. 41 (2021) 2121–2126. doi: 10.6023/cjoc202010006
17. [17]
  X. Fang, W. Wang, X. Yang, F. Wu. Chin. J. Org. Chem. 41 (2021) 412–417. doi: 10.6023/cjoc202007028
18. [18]
  N. Xu, X. Jin, K. Suzuki, K. Yamaguchi, N. Mizuno, New J. Chem. 40 (2016) 4865–4869. doi: 10.1039/C5NJ03579A
19. [19]
  J. Hu, Y. Yang, Z. Lou, C. Ni, J. Hu, Chin. J. Chem. 36 (2018) 1202–1208. doi: 10.1002/cjoc.201800426
20. [20]
  H. Liu, Z. Yang, Z. Pan, Org. Lett. 16 (2014) 5902–5905. doi: 10.1021/ol502900j
21. [21]
  D.A. Nicewicz, D.W.C. MacMillan, Science 322 (2008) 77–80. doi: 10.1126/science.1161976
22. [22]
  J. Jin, D.W.C. MacMillan, Nature 525 (2015) 87–90. doi: 10.1038/nature14885
23. [23]
  E.B. Corcoran, M.T. Pirnot, S. Lin, et al., Science 353 (2016) 279–283. doi: 10.1126/science.aag0209
24. [24]
  I. Ghosh, T. Ghosh, J.I. Bardagi, B. König, Science 346 (2014) 725–728. doi: 10.1126/science.1258232
25. [25]
  A. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 436 (2005) 1139–1140. doi: 10.1038/nature03955
26. [26]
  M. Silvi, C. Verrier, Y.P. Rey, L. Buzzetti, P. Melchiorre, Nat. Chem. 9 (2017) 868–873. doi: 10.1038/nchem.2748
27. [27]
  M. Yang, H. Han, H. Jiang, et al., Chin. Chem. Lett. 32 (2021) 3535–3538. doi: 10.1016/j.cclet.2021.05.007
28. [28]
  D. Yang, Q. Yan, E. Zhu, J. Lv, W.M. He. Chin. Chem. Lett. 33 (2022) 1798–1816. doi: 10.1016/j.cclet.2021.09.068
29. [29]
  Z. Yan, B. Sun, P. Huang, et al., Chin. Chem. Lett. 33 (2022) 1997–2000. doi: 10.1016/j.cclet.2021.09.067
30. [30]
  Z.Y. Bo, S.S. Yan, T.Y. Gao, et al., Chin. J. Catal. 43 (2022) 2388–2394. doi: 10.1016/S1872-2067(22)64140-8
31. [31]
  J. Twilton, C. Le, P. Zhang, et al., Nat. Rev. Chem. 1 (2017) 0052. doi: 10.1038/s41570-017-0052
32. [32]
  L. Marzo, S.K. Pagire, O. Reiser, B. Kӧnig, Angew. Chem. Int. Ed. 57 (2014) 10034–10072.
33. [33]
  J.M.R. Narayanam, C.R.J. Stephenson, Chem. Soc. Rev. 40 (2011) 102–113. doi: 10.1039/B913880N
34. [34]
  K.L. Skubi, T.R. Blum, T.P. Yoon, Chem. Rev. 116 (2016) 10035–10074. doi: 10.1021/acs.chemrev.6b00018
35. [35]
  C.K. Prier, D.A. Rankic, D.W.C. MacMillan, Chem. Rev. 113 (2013) 5322–5363. doi: 10.1021/cr300503r
36. [36]
  J.C. Tellis, D.N. Primer, G.A. Molander, Science 345 (2014) 433–436. doi: 10.1126/science.1253647
37. [37]
  C.P. Johnston, R.T. Smith, S. Allmendinger, D.W.C. MacMillan, Nature 536 (2016) 322–325. doi: 10.1038/nature19056
38. [38]
  N.A. Romero, D.A. Nicewicz, Chem. Rev. 116 (2016) 10075–10166. doi: 10.1021/acs.chemrev.6b00057
39. [39]
  X. Zhu, Y. Liu, C. Liu, H. Yang, H. Fu, Green Chem. 22 (2020) 4357–4363. doi: 10.1039/d0gc00383b
40. [40]
  X. Zhu, C. Liu, Y. Liu, H. Yang, H. Fu, Chem. Commun. 56 (2020) 12443–12446. doi: 10.1039/d0cc05799a
41. [41]
  Y. Qin, T. Zhang, H.Y.V. Ching, G.S. Raman, S. Das, Chem. 8 (2022) 2472–2484. doi: 10.1016/j.chempr.2022.06.002
42. [42]
  K.J. Liu, Z. Wang, L.H. Lu, et al., Green Chem. 23 (2021) 496–500. doi: 10.1039/d0gc02663h
43. [43]
  P. Xie, C. Xue, C. Wang, D. Du, S. Shi, Org. Chem. Front. 8 (2021) 3427–3433. doi: 10.1039/d1qo00438g
44. [44]
  Y.X. Chen, J.T. He, M.C. Wu, et al., Yang, Org. Lett. 24 (2022) 3920–3925. doi: 10.1021/acs.orglett.2c01192
45. [45]
  C.L. Zeng, H. Wang, D. Gao, et al., Org. Lett. 24 (2022) 3244–3248. doi: 10.1021/acs.orglett.2c01032
46. [46]
  K. McKeage, G.M. Keating, Drugs 71 (2011) 1917–1946. doi: 10.2165/11208090-000000000-00000
47. [47]
  A. Yassin, K. AlRumaihi, R. Alzubaidi, S. Alkadhi, A.A. Ansari, Aging Male 22 (2019) 219–227. doi: 10.1080/13685538.2018.1524456
1. [1]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
2. [2]
  Yan Wang , Jiaqi Zhang , Xiaofeng Wu , Sibo Wang , Masakazu Anpo , Yuanxing Fang . Elucidating oxygen evolution and reduction mechanisms in nitrogen-doped carbon-based photocatalysts. Chinese Chemical Letters, 2025, 36(2): 110439-. doi: 10.1016/j.cclet.2024.110439
3. [3]
  Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
4. [4]
  Qiang Zhang , Weiran Gong , Huinan Che , Bin Liu , Yanhui Ao . S doping induces to promoted spatial separation of charge carriers on carbon nitride for efficiently photocatalytic degradation of atrazine. Chinese Journal of Structural Chemistry, 2023, 42(12): 100205-100205. doi: 10.1016/j.cjsc.2023.100205
5. [5]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
6. [6]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
7. [7]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
8. [8]
  Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
9. [9]
  Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
10. [10]
  Yanghanbin Zhang , Dongxiao Wen , Wei Sun , Jiahe Peng , Dezhong Yu , Xin Li , Yang Qu , Jizhou Jiang . State-of-the-art evolution of g-C3N4-based photocatalytic applications: A critical review. Chinese Journal of Structural Chemistry, 2024, 43(12): 100469-100469. doi: 10.1016/j.cjsc.2024.100469
11. [11]
  Tianhao Li , Wenguang Tu , Zhigang Zou . In situ photocatalytically enhanced thermogalvanic cells for electricity and hydrogen production. Chinese Journal of Structural Chemistry, 2024, 43(1): 100195-100195. doi: 10.1016/j.cjsc.2023.100195
12. [12]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
13. [13]
  Yue Pan , Wenping Si , Yahao Li , Haotian Tan , Ji Liang , Feng Hou . Promoting exciton dissociation by metal ion modification in polymeric carbon nitride for photocatalysis. Chinese Chemical Letters, 2024, 35(12): 109877-. doi: 10.1016/j.cclet.2024.109877
14. [14]
  Jia-Cheng Hou , Wei Cai , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Recent advances in semi-heterogenous photocatalysis in organic synthesis. Chinese Chemical Letters, 2025, 36(2): 110469-. doi: 10.1016/j.cclet.2024.110469
15. [15]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
16. [16]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
17. [17]
  Yan Fan , Jiao Tan , Cuijuan Zou , Xuliang Hu , Xing Feng , Xin-Long Ni . Unprecedented stepwise electron transfer and photocatalysis in supramolecular assembly derived hybrid single-layer two-dimensional nanosheets in water. Chinese Chemical Letters, 2025, 36(4): 110101-. doi: 10.1016/j.cclet.2024.110101
18. [18]
  Lihua Ma , Song Guo , Zhi-Ming Zhang , Jin-Zhong Wang , Tong-Bu Lu , Xian-Shun Zeng . Sensitizing photoactive metal–organic frameworks via chromophore for significantly boosting photosynthesis. Chinese Chemical Letters, 2024, 35(5): 108661-. doi: 10.1016/j.cclet.2023.108661
19. [19]
  Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H₂O₂ photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
20. [20]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(518)
HTML views(21)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142