Citation: Tingting Zhang, Jing Zhang. Photocatalyzed hydrogen transfer enabled three-component radical cascade reactions: Direct access to thioesters from primary alcohols, elemental sulfur and alkenes[J]. Chinese Chemical Letters, ;2026, 37(1): 111131. doi: 10.1016/j.cclet.2025.111131 shu

Photocatalyzed hydrogen transfer enabled three-component radical cascade reactions: Direct access to thioesters from primary alcohols, elemental sulfur and alkenes

Tingting Zhang ,
Jing Zhang ^*,

The Institute for Advanced Studies, Wuhan University, Wuhan 430072, China

jing.zhang.nd@gmail.com

Received Date: 29 November 2024
Revised Date: 15 March 2025
Accepted Date: 20 March 2025
Available Online: 20 March 2025

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The development of catalytic multicomponent reactions for constructing complex organic scaffolds from readily accessible commodity chemicals is a key pursuit in contemporary synthetic chemistry. Current methods for synthesizing thioesters primarily rely on the acylation of thiols, which produces substantial waste and requires malodorous, unstable sulfur sources. In this work, we introduce a photocatalyzed hydrogen transfer strategy that enables a three-component synthesis of thioesters using abundant primary alcohols, easily available alkenes and elemental sulfur under mild conditions. This protocol demonstrates broad applicability and high chemo- and regioselectivity for both primary alcohols and alkenes, highlighting the advantage and potential of photo-mediated hydrogen transfer in facilitating multicomponent reactions using primary alcohol and elemental sulfur feedstocks.
- Photocatalysis,
- Hydrogen atom transfer,
- Primary alcohol,
- Thioester,
- Elemental sulfur
1. [1]
  Y. Kanda, T. Ashizawa, S. Kakita, et al., J. Med. Chem. 42 (1999) 1330–1332. doi: 10.1021/jm9900366
2. [2]
  N. Wang, P. Saidhareddy, X. Jiang, Nat. Prod. Rep. 37 (2020) 246–275. doi: 10.1039/c8np00093j
3. [3]
  K. Taori, V.J. Paul, H. Luesch, J. Am. Chem. Soc. 130 (2008) 1806–1807. doi: 10.1021/ja7110064
4. [4]
  X.L. Liu, Y. Shi, J.S. Kang, P. Oelschlaeger, K.W. Yang, ACS Med. Chem. Lett. 6 (2015) 660–664. doi: 10.1021/acsmedchemlett.5b00098
5. [5]
  S. Aksakal, R. Aksakal, C.R. Becer, Poly. Chem. 9 (2018) 4507–4516. doi: 10.1039/c8py00872h
6. [6]
  N. Martin, V. Neelz, H.E. Spinnler, Food Qual. Prefer. 15 (2004) 247–257. doi: 10.1016/S0950-3293(03)00065-X
7. [7]
  F. Pietrocola, L. Galluzzi, J.M. Bravo-San Pedro, F. Madeo, G. Kroemer, Cell Metab. 21 (2015) 805–821. doi: 10.1016/j.cmet.2015.05.014
8. [8]
  J. Franke, C. Hertweck, Cell Chem. Biol. 23 (2016) 1179–1192. doi: 10.1016/j.chembiol.2016.08.014
9. [9]
  V. Agouridas, O.E. Mahdi, V. Diemer, et al., Chem. Rev. 119 (2019) 7328–7443. doi: 10.1021/acs.chemrev.8b00712
10. [10]
  S. Sikandar, A.F. Zahoor, S. Naheed, et al., Mol. Divers. 26 (2022) 589–628. doi: 10.1007/s11030-021-10194-7
11. [11]
  S. Iimura, K. Manabe, S. Kobayashi, Chem. Commun. 38 (2002) 94–95.
12. [12]
  H. Wang, Z. Liu, A. Das, et al., Nat. Synth. 2 (2023) 1116–1126. doi: 10.1038/s44160-023-00353-z
13. [13]
  C. Santi, B. Battistelli, L. Testaferri, M. Tiecco, Green Chem. 14 (2012) 1277–1280. doi: 10.1039/c2gc16541d
14. [14]
  M. Kazemi, L. Shiri, J. Sulfur Chem. 36 (2015) 613–623. doi: 10.1080/17415993.2015.1075023
15. [15]
  T. Uno, T. Inokuma, Y. Takemoto, Chem. Commun. 48 (2012) 1901–1903. doi: 10.1039/c2cc17183j
16. [16]
  C.L. Yi, Y.T. Huang, C.F. Lee, Green Chem. 15 (2013) 2476–2484. doi: 10.1039/c3gc40946e
17. [17]
  V. Zoufal, S. Mairinger, M. Brackhan, et al., J. Nucl. Med. 61 (2020) 1050–1057. doi: 10.2967/jnumed.119.237198
18. [18]
  N. Kosaric, Z. Duvnjak, A. Farkas, et al., Ethanol, in: C. Ley, B. Elvers, et al. (Eds.), Ullmann’s Encyclopedia of Industrial Chemistry, seventh ed., Wiley-VCH, 2011, pp. 333–403.
19. [19]
  J. Ott, V. Gronemann, F. Pontzen, et al., Methanol, in: C. Ley, B. Elvers, et al. (Eds.), Ullmann’s Encyclopedia of Industrial Chemistry, 7th ed., Wiley-VCH, 2011, pp. 1–27.
20. [20]
  V.J. Roy, P.P. Sen, S.R. Roy, J. Org. Chem. 86 (2021) 16965–16976. doi: 10.1021/acs.joc.1c02111
21. [21]
  X. Zhu, Y. Shi, H. Mao, Y. Cheng, C. Zhu, Adv. Synth. Catal. 355 (2013) 3558–3562. doi: 10.1002/adsc.201300584
22. [22]
  J. Luo, M. Rauch, L. Avram, et al., Nat. Catal. 3 (2020) 887–892. doi: 10.1038/s41929-020-00514-9
23. [23]
  M. Rauch, J. Luo, L. Avram, Y. Ben-David, D. Milstein, ACS Catal. 11 (2021) 2795–2807. doi: 10.1021/acscatal.1c00418
24. [24]
  T.V. Choudhary, J. Malandra, J. Green, S. Parrott, B. Johnson, Angew. Chem. Int. Ed. 45 (2006) 3299–3303. doi: 10.1002/anie.200503660
25. [25]
  H. Liu, X. Jiang, Chem. Asian J. 8 (2013) 2546–2563. doi: 10.1002/asia.201300636
26. [26]
  T.B. Nguyen, Adv. Synth. Catal. 362 (2020) 3448–3484. doi: 10.1002/adsc.202000535
27. [27]
  H. Huang, G.-J. Deng, S. Liu, Synlett 32 (2021) 142–158. doi: 10.1364/ol.409729
28. [28]
  M. Wang, Z. Dai, X. Jiang, Nat. Commun. 10 (2019) 2661. doi: 10.1038/s41467-019-10651-w
29. [29]
  A. Porey, S.O. Fremin, S. Nand, et al., ACS Catal. 14 (2024) 6973–6980. doi: 10.1021/acscatal.4c01289
30. [30]
  T.B. Nguyen, Asian J. Org. Chem. 6 (6) (2017) 477–491. doi: 10.1002/ajoc.201700011
31. [31]
  T.B. Nguyen, Adv. Synth. Catal. 359 (2017) 1066–1130. doi: 10.1002/adsc.201601329
32. [32]
  S. Murakami, T. Nanjo, Y. Takemoto, Org. Lett. 23 (2021) 7650–7655 2021. doi: 10.1021/acs.orglett.1c02904
33. [33]
  H. Tang, M. Zhang, Y. Zhang, et al., J. Am. Chem. Soc. 145 (2023) 5846–5854. doi: 10.1021/jacs.2c13157
34. [34]
  S. Protti, M. Fagnoni, D. Ravelli, ChemCatChem 7 (2015) 1516–1523. doi: 10.1002/cctc.201500125
35. [35]
  D. Ravelli, M. Fagnoni, T. Fukuyama, T. Nishikawa, I. Ryu, ACS Catal. 8 (2018) 701–713. doi: 10.1021/acscatal.7b03354
36. [36]
  L. Capaldo, D. Ravelli, M. Fagnoni, Chem. Rev. 122 (2022) 1875–1924. doi: 10.1021/acs.chemrev.1c00263
37. [37]
  T. Yamase, N. Takabayashi, M. Kaji, J. Chem. Soc., Dalton Trans. 1984 (1984) 793–799.
38. [38]
  J.J. Zhong, W.P. To, Y. Liu, W. Lu, C.M. Che, Chem. Sci. 10 (2019) 4883–4889. doi: 10.1039/c8sc05600e
39. [39]
  X.J. Yang, Y.W. Zheng, L.Q. Zheng, et al., Green Chem. 21 (2019) 1401–1405. doi: 10.1039/c8gc03828g
40. [40]
  Y.L. Liu, Y.J. Ouyang, H. Zheng, H. Liu, W.T. Wei, Chem. Commun. 57 (2021) 6111–6120. doi: 10.1039/d1cc02112e
41. [41]
  C. Raviola, S. Protti, D. Ravelli, M. Fagnoni, Green Chem. 21 (2019) 748–764. doi: 10.1039/c8gc03810d
42. [42]
  M.A. Theodoropoulou, N.F. Nikitas, C.G. Kokotos, Bellstein J. Org. Chem. 16 (2020) 833–857. doi: 10.3762/bjoc.16.76
43. [43]
  A. Banerjee, Z. Lei, M.Y. Ngai, Synthesis 51 (2019) 303–333. doi: 10.1055/s-0037-1610329
44. [44]
  D.J. Abrams, J.G. West, E.J. Sorensen, Chem. Sci. 8 (2017) 1954–1959. doi: 10.1039/C6SC04607J
45. [45]
  W.E. Vaughan, F.F. Rust, J. Org. Chem. 7 (1942) 472–476. doi: 10.1021/jo01200a004
46. [46]
  K.I. Sugimoto, W. Ando, S. Oae, Bull. Chem. Soc. Jpn. 37 (1964) 365–368. doi: 10.1246/bcsj.37.365
47. [47]
  T. Yamase, T. Usami, J. Chem. Soc., Dalton Trans. 1988 (1988) 183–190.
48. [48]
  I. Ryu, A. Tani, T. Fukuyama, et al., Angew. Chem. Int. Ed. 50 (2011) 1869–1872. doi: 10.1002/anie.201004854
49. [49]
  Y. Kuang, H. Cao, H. Tang, et al., Chem. Sci. 11 (2020) 8912–8918. doi: 10.1039/d0sc02661a
50. [50]
  D. Dondi, M. Fagnoni, A. Albini, Chem. Eur. J. 12 (2006) 4153–4163. doi: 10.1002/chem.200501216
51. [51]
  V.D. Waele, O. Poizat, M. Fagnoni, A. Bagno, D. Ravelli, ACS Catal. 6 (2016) 7174–7182. doi: 10.1021/acscatal.6b01984
52. [52]
  T. Fukuyama, K. Yamada, T. Nishikawa, et al., Chem. Lett. 47 (2018) 207–209. doi: 10.1246/cl.171068
53. [53]
  K. Yamada, T. Fukuyama, S. Fujii, et al., Chem. Eur. J. 23 (2017) 8615–8618. doi: 10.1002/chem.201701865
54. [54]
  A.W. Horton, Dehydrogenation of alcohols with sulfur, Patent, US2522676, 1950.
55. [55]
  B. Zheng, L. Zhong, X. Wang, et al., Nat. Commun. 15 (2024) 5507. doi: 10.1038/s41467-024-49374-y
56. [56]
  A. Prieto, M. Taillefer, Org. Lett. 23 (2021) 1484–1488. doi: 10.1021/acs.orglett.1c00189
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