Citation: Kaichuan Yan, Hua He, Jianglian Li, Yi Luo, Ruizhi Lai, Li Guo, Yong Wu. Blue light-promoted cyclopropenizations of N-tosylhydrazones in water[J]. Chinese Chemical Letters, ;2021, 32(12): 3984-3987. doi: 10.1016/j.cclet.2021.05.031 shu

Blue light-promoted cyclopropenizations of N-tosylhydrazones in water

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

guoli@scu.edu.cn

wyong@scu.edu.cn

Received Date: 10 March 2021
Revised Date: 10 May 2021
Accepted Date: 16 May 2021
Available Online: 24 May 2021

Figures(6)

Carbene transfer reactions play an important role in the field of organic synthesis because of their ability to construct a variety of molecules. Herein, we reported on blue light-induced cyclopropenizations of N-tosylhydrazones in water, which avoids the use of expensive metal-based catalysts and toxic organic solvents. This metal-free and operationally simple methodology enable highly efficient cyclopropenizations, X-H insertion reactions, and cyclopropanation under mild reaction conditions.
- N-Tosylhydrazone,
- Carbene,
- Metal-free,
- Cyclopropenization,
- Cyclopropanation
1. [1]
  Y. Zhou, F. Ye, X. Wang, et al., J. Org. Chem. 80 (2015) 6109–6118. doi: 10.1021/acs.joc.5b00629
2. [2]
  H. Zhao, K. Yang, H. Zheng, et al., Org. Lett. 17 (2015) 5744–5747. doi: 10.1021/acs.orglett.5b02783
3. [3]
  S. Chen, J. Wang, Chem. Commun. (Camb) (2008) 4198–4200. doi: 10.1039/b806970k
4. [4]
  S.F. Zhu, Q.L. Zhou, Nat. Sci. Rev. 1 (2014) 580–603. doi: 10.1093/nsr/nwu019
5. [5]
  Z. Zhang, Z. Sheng, W. Yu, et al., Nat. Chem. 9 (2017) 970–976. doi: 10.1038/nchem.2789
6. [6]
  Z. Song, Y. Wu, T. Xin, et al., Chem. Commun. (Camb) 52 (2016) 6079–6082. doi: 10.1039/C6CC02641A
7. [7]
  Z. Sheng, Z.K. Zhang, C.H. Chu, et al., Tetrahedron 73 (2017) 4011–4022.
8. [8]
  R. Shang, L. Ilies, E. Nakamura, Chem. Rev. 117 (2017) 9086–9139. doi: 10.1021/acs.chemrev.6b00772
9. [9]
  M. Liao, L. Peng, J. Wang, Org. Lett. 10 (2008) 693–696. doi: 10.1021/ol703058p
10. [10]
  D.M. Hodgson, F.Y.T.M. Pierard, P.A. Stupple, Chem. Soc. Rev. 30 (2001) 50–61.
11. [11]
  K.J. Hock, R.M. Koenigs, Angew. Chem. Int. Ed. 56 (2017) 13566–13568. doi: 10.1002/anie.201707092
12. [12]
  S.F. Zhu, Q.L. Zhou, Acc Chem. Res. 45 (2012) 1365–1377. doi: 10.1021/ar300051u
13. [13]
  S.F. Zhu, B. Xu, G.P. Wang, et al., J. Am. Chem. Soc. 134 (2012) 436–442. doi: 10.1021/ja2084493
14. [14]
  Y. Zhang, Y. Yao, L. He, et al., Adv. Syn. Catal. 359 (2017) 2754–2761. doi: 10.1002/adsc.201700572
15. [15]
  B. Xu, S.F. Zhu, X.L. Xie, et al., Angew. Chem. Int. Ed. 50 (2011) 11483–11486. doi: 10.1002/anie.201105485
16. [16]
  F. Tan, X. Liu, X. Hao, et al., ACS Catal. 6 (2016) 6930–6934. doi: 10.1021/acscatal.6b02184
17. [17]
  C. Qin, H.M. Davies, J. Am. Chem. Soc. 136 (2014) 9792–9796. doi: 10.1021/ja504797x
18. [18]
  Z. Hou, J. Wang, P. He, et al., Angew. Chem. Int. Ed. 49 (2010) 4763–4766. doi: 10.1002/anie.201001686
19. [19]
  X. Xu, M.P. Doyle, Acc Chem. Res. 47 (2014) 1396–1405. doi: 10.1021/ar5000055
20. [20]
  A. Padwa, Chem. Soc. Rev. 38 (2009) 3072–3081. doi: 10.1039/b816701j
21. [21]
  L.A. Lopez, J. Gonzalez, Org. Biomol. Chem. 17 (2019) 646–654. doi: 10.1039/c8ob02676a
22. [22]
  K. Dong, C. Pei, Q. Zeng, et al., Chem. Commun. (Camb) 55 (2019) 6393–6396. doi: 10.1039/c9cc02257k
23. [23]
  H.M.L. Davies, S.J. Hedley, Chem. Soc. Rev. 36(2007). 1109–1119. doi: 10.1039/b607983k
24. [24]
  Q.Q. Cheng, Y. Deng, M. Lankelma, et al., Chem. Soc. Rev. 46 (2017) 5425–5443. doi: 10.1039/C7CS00324B
25. [25]
  Y. Yang, X. Wang, Y. Li, et al., Angew. Chem. Int. Ed. 54 (2015) 15400–15404. doi: 10.1002/anie.201508702
26. [26]
  Y. Wu, Z. Chen, Y. Yang, et al., J. Am. Chem. Soc. 140 (2018) 42–45. doi: 10.1021/jacs.7b10349
27. [27]
  J. Wang, M. Wang, K. Chen, et al., Org. Lett. 18 (2016) 1178–1181. doi: 10.1021/acs.orglett.6b00310
28. [28]
  B. Li, B. Zhang, X. Zhang, et al., Chem. Commun. (Camb) 53 (2017) 1297–1300. doi: 10.1039/C6CC08377C
29. [29]
  H.M. Davies, J.R. Manning, Nature 451 (2008) 417–424. doi: 10.1038/nature06485
30. [30]
  Y. Xia, J. Wang, Chem. Soc. Rev. 46 (2017) 2306–2362. doi: 10.1039/C6CS00737F
31. [31]
  M. Jia, S. Ma, Angew. Chem. Int. Ed. 55 (2016) 9134–9166. doi: 10.1002/anie.201508119
32. [32]
  J. Yang, J. Wang, H. Huang, et al., Org. Lett. 21 (2019) 2654–2657. doi: 10.1021/acs.orglett.9b00647
33. [33]
  T. Xiao, M. Mei, Y. He, et al., Chem. Commun. (Camb) 54 (2018) 8865–8868. doi: 10.1039/c8cc04609c
34. [34]
  R. Hommelsheim, Y. Guo, Z. Yang, et al., Angew. Chem. Int. Ed. 58(2019). 1203–1207. doi: 10.1002/anie.201811991
35. [35]
  F. He, F. Li, R.M. Koenigs, J. Org. Chem. 85 (2020) 1240–1246. doi: 10.1021/acs.joc.9b02605
36. [36]
  Y. Guo, T.V. Nguyen, R.M. Koenigs, Org. Lett. 21 (2019) 8814–8818. doi: 10.1021/acs.orglett.9b03453
37. [37]
  C. Empel, F.W. Patureau, R.M. Koenigs, J. Org. Chem. 84 (2019) 11316–11322. doi: 10.1021/acs.joc.9b01753
38. [38]
  W. Xiong, C. Qi, H. He, et al., Angew. Chem. Int. Ed. 54 (2015) 3084–3087. doi: 10.1002/anie.201410605
39. [39]
  M.C. Perez-Aguilar, C. Valdes, Angew. Chem. Int. Ed. 51 (2012) 5953–5957. doi: 10.1002/anie.201200683
40. [40]
  Z. Liu, Q. Li, P. Liao, et al., Chemistry (Easton) 23 (2017) 4756–4760. doi: 10.1002/chem.201605335
41. [41]
  J. Barluenga, C. Valdes, Angew. Chem. Int. Ed. 50 (2011) 7486–7500. doi: 10.1002/anie.201007961
42. [42]
  J. Aziz, J.D. Brion, A. Hamze, et al., Adv. Syn. Catal. 355 (2013) 2417–2429. doi: 10.1002/adsc.201300466
43. [43]
  Y. Xu, G. Lv, K. Yan, et al., Chem. Asian J. 15 (2020) 1945–1947. doi: 10.1002/asia.202000378
44. [44]
  S. Jana, F. Li, C. Empel, et al., Chemistry (Easton) 26 (2020) 2586–2591. doi: 10.1002/chem.201904994
45. [45]
  Z.B. Zhu, Y. Wei, M. Shi, Chem. Soc. Rev. 40 (2011) 5534–5563. doi: 10.1039/c1cs15074j
46. [46]
  I. Marek, S. Simaan, A. Masarwa, Angew. Chem. Int. Ed. 46 (2007) 7364–7376. doi: 10.1002/anie.200604774
47. [47]
  M.J. Gonzalez, J. Gonzalez, L.A. Lopez, et al., Angew. Chem. Int. Ed. 54 (2015) 12139–12143. doi: 10.1002/anie.201505954
48. [48]
  A. Archambeau, F. Miege, C. Meyer, et al., Acc Chem. Res. 48 (2015) 1021–1031. doi: 10.1021/acs.accounts.5b00016
49. [49]
  B. Morandi, E.M. Carreira, Angew. Chem. Int. Ed. 49 (2010) 4294–4296. doi: 10.1002/anie.201000787
50. [50]
  T. Goto, K. Takeda, N. Shimada, et al., Angew. Chem. Int. Ed. Engl, 50 (2011) 6803–6808. doi: 10.1002/anie.201101905
51. [51]
  J.F. Briones, H.M. Davies, J. Am. Chem. Soc. 134 (2012) 11916–11919. doi: 10.1021/ja304506g
52. [52]
  W.Y. Yu, Y.T. Tsoi, Z. Zhou, et al., Org. Lett. 11 (2009) 469–472. doi: 10.1021/ol8026076
53. [53]
  J. Barluenga, M. Tomas-Gamasa, F. Aznar, et al., Ang. Chem. Int. Ed. 49 (2010) 4993–4996. doi: 10.1002/anie.201001704
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