Citation: Ge Wu, Xueying Zhou, Caihong Wang. Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids[J]. Chinese Chemical Letters, ;2022, 33(10): 4531-4535. doi: 10.1016/j.cclet.2022.01.044 shu

Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids

Ge Wu ^{a, b, *,} ,
Xueying Zhou ^a ,
Caihong Wang ^a

a.
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

wuge@wmu.edu.cn

Received Date: 4 November 2021
Revised Date: 12 January 2022
Accepted Date: 16 January 2022
Available Online: 23 January 2022

Figures(6)

A novel and efficient copper-catalyzed decarboxylative alkynylselenation of indoles with Se powder and propiolic acids has been developed. The outstanding advantages of this protocol not only nicely avoid the use of prefabricated arylselenation reagent and address the facile over-selention issues, but also enrich the chemistry of selenium powder. Importantly, this reaction could be extended to pyrrole, and the practical utility of this transformation has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
- Se powder,
- Copper catalysis,
- Decarboxylation,
- Multi-component reaction,
- Propiolic acids
1. [1]
  G. Mugesh, W.W. Mont, H. Sies, Chem. Rev. 101 (2001) 2125-2180. doi: 10.1021/cr000426w
2. [2]
  C.W. Nogueira, G. Zeni, J.B.T. Rocha, Chem. Rev. 104 (2004) 6255-6285. doi: 10.1021/cr0406559
3. [3]
  J.V. Comasseto, P.H. Menezes, H.A. Stefani, G. Zeni, A.L. Braga, Tetrahedron 52 (1996) 9687-9702. doi: 10.1016/0040-4020(96)00505-4
4. [4]
  M.J. Dabdoub, M.L. Begnini, P.G. G Jr, Tetrahedron 54 (1998) 2371-2400. doi: 10.1016/S0040-4020(98)00014-3
5. [5]
  A. Sun, X. Huang, Synthesis (Mass) 6 (2000) 775-777.
6. [6]
  M. Tiecco, L. Testaferri, A. Temperini, et al., Eur. J. Org. Chem. (2004) 3447-3458.
7. [7]
  F. Manarin, J.A. Roehrs, R.M. Gay, et al., J. Org. Chem. 74 (2009) 2153-2162. doi: 10.1021/jo802736e
8. [8]
  A.L. Stein, F.N. Bilheri, G. Zeni, Chem. Commun. 51 (2015) 15522-15525. doi: 10.1039/C5CC06347G
9. [9]
  A. Sharma, R.S. Schwab, A.L. Braga, T. Barcellos, M.W. Paixão, Tetrahedron Lett. 49 (2008) 5172-5174. doi: 10.1016/j.tetlet.2008.06.071
10. [10]
  S. Ahammed, S. Bhadra, D. Kundu, B. Sreedhar, B.C. Ranu, Tetrahedron 68 (2012) 10542-10549. doi: 10.1016/j.tet.2012.08.046
11. [11]
  T. Hayama, S. Tomoda, Y. Takeuchi, Y. Nomura, Chem. Lett. (1982) 1249-1250.
12. [12]
  A.L. Braga, C.C. Silviera, A. Reckziegel, P.H. Menezes, Tetrahedron Lett. 34 (1993) 8041-8042. doi: 10.1016/S0040-4039(00)61445-4
13. [13]
  R.J. Cohen, D.L. Fox, R.N. Salvatore, J. Org. Chem. 69 (2004) 4265-4268. doi: 10.1021/jo0401265
14. [14]
  L.W. Bieber, M.F. da Silva, P.H. Menezes, Tetrahedron Lett. 45 (2004) 2735-2737. doi: 10.1016/j.tetlet.2004.02.042
15. [15]
  D.S. Rampon, R. Giovenardi, T.L. Silva, et al., Eur. J. Org. Chem. (2011) 7066-7070. doi: 10.1002/ejoc.201101245
16. [16]
  B. Movassagh, M. Navidi, Chin. Chem. Lett. 23 (2012) 1035-1038. doi: 10.1016/j.cclet.2012.06.036
17. [17]
  M. Godoi, E.W. Ricardo, T.E. Frizon, et al., Tetrahedron 68 (2012) 10426-10430. doi: 10.1016/j.tet.2012.08.086
18. [18]
  B. Movassagh, A. Yousefi, B.Z. Momeni, S. Heydari, Synlett 25 (2014) 1385-1390. doi: 10.1055/s-0033-1341277
19. [19]
  B. Mohan, J.C. Park, K.H. Park, ChemCatChem 8 (2016) 2345-2350. doi: 10.1002/cctc.201600280
20. [20]
  N. Mukherjee, D. Kundu, B.C. Ranu, Adv. Synth. Catal. 359 (2017) 329-338. doi: 10.1002/adsc.201600933
21. [21]
  D. Kundu, N. Mukherjee, B.C. Ranu, RSC Adv. 3 (2013) 117-125. doi: 10.1039/C2RA22415A
22. [22]
  B. Mohan, C. Yoon, S. Jang, K.H. ParK, ChemCatChem 7 (2015) 405-412. doi: 10.1002/cctc.201402867
23. [23]
  S. Rui, L. Lei, Sci. China: Chem. 54 (2011) 1670-1687. doi: 10.1007/s11426-011-4381-0
24. [24]
  K. Park, S. Lee, RSC Adv. 3 (2013) 14165-14182. doi: 10.1039/c3ra41442f
25. [25]
  M.A. Idris, S. Lee, Synthesis (Mass) 52 (2020) 2277-2298. doi: 10.1055/s-0040-1707600
26. [26]
  C. Chen, J. Wu, G. Yan, D. Huang, Tetrahedron Lett. 61 (2020) 151415-151430. doi: 10.1016/j.tetlet.2019.151415
27. [27]
  F. Cui, J. Chen, Z. Mo, et al., Org. Lett. 20 (2018) 925-929. doi: 10.1021/acs.orglett.7b03734
28. [28]
  A.V. Moro, C.W. Nogueira, N.B.V. Barbosa, et al., J. Org. Chem. 70 (2005) 5257-5268. doi: 10.1021/jo050448o
29. [29]
  M. Godoi, D.G. Liz, E.W. Ricardo, et al., Tetrahedron 70 (2014) 3349-3354. doi: 10.1016/j.tet.2013.09.095
30. [30]
  A.A. Heredia, A.B. Peñéñory, Beilstein J. Org. Chem. 13 (2017) 910-918. doi: 10.3762/bjoc.13.92
31. [31]
  J. Chen, S.X. Su, D.C. Hu, et al., Asian J. Org. Chem. 7 (2018) 892-896. doi: 10.1002/ajoc.201800086
32. [32]
  Y. Wang, L. Liu, G. Wang, H. Ouyang, Y. Li, Green Chem. 20 (2018) 604-608. doi: 10.1039/C7GC03267F
33. [33]
  D. Hu, M. Liu, H. Wu, W. Gao, G. Wu, Org. Chem. Front. 5 (2018) 1352-1355. doi: 10.1039/C8QO00066B
34. [34]
  X. Gao, L. Tang, L. Huang, et al., Org. Lett. 21 (2019) 745-748. doi: 10.1021/acs.orglett.8b03980
35. [35]
  R.A. Rather, T. Ara, Tetrahddron 96 (2021) 132386-132389. doi: 10.1016/j.tet.2021.132386
36. [36]
  D.X. Liu, F.L. Li, H.X. Li, et al., Eur. J. Org. Chem. (2014) 4817-4822.
37. [37]
  M. Zeng, J.W. Xue, H. Jiang, et al., J. Org. Chem. 86 (2021) 8333-8350. doi: 10.1021/acs.joc.1c00762
38. [38]
  Z. He, R. Zhang, M. Hu, et al., Chem. Sci. 4 (2013) 3478-3483. doi: 10.1039/c3sc51613j
39. [39]
  Y. Li, Y. Wang, T. Yang, Z. Lin, X. Jiang, Green Chem. 23 (2021) 2986-2991. doi: 10.1039/D0GC04407E
40. [40]
  W.J. Yoo, M.G. Capdevila, X. Du, S. Kobayashi, Org. Lett. 14 (2012) 5326-5329. doi: 10.1021/ol3025082
41. [41]
  Y. Li, J.Q. Shang, X.X. Wang, et al., Org. Lett. 21 (2019) 2227-2230. doi: 10.1021/acs.orglett.9b00520
42. [42]
  I.S. Young, P.D. Thornton, A. Thompson, Nat. Prod. Rep. 27 (2010) 1801-1839. doi: 10.1039/c0np00014k
43. [43]
  A.H. Yu, R.H. Qiu, N.Y. Tan, L.F. Peng, X.H. Xu, Chin. Chem. Lett. 22 (2011) 687-690. doi: 10.1016/j.cclet.2010.12.050
44. [44]
  B.L. Ryland, S.D. McCann, T.C. Brunold, S.S. Stahl, J. Am. Chem. Soc. 136 (2014) 12166-12173. doi: 10.1021/ja5070137
45. [45]
  X. Li, F. Yang, Y. Wu, Y. Wu, Org. Lett. 16 (2014) 992-995. doi: 10.1021/ol4037242
46. [46]
  A.E. King, L.M. Huffman, A. Casitas, et al., J. Am. Chem. Soc. 132 (2010) 12068-12073. doi: 10.1021/ja1045378
47. [47]
  L. Jiang, J. Qian, W. Yi, et al., Angew. Chem. Int. Ed. 54 (2015) 14965-14969. doi: 10.1002/anie.201508495
48. [48]
  Z. Wang, Z. Yin, X.F. Wu, Chem. Commun. 54 (2018) 4798-4801. doi: 10.1039/C8CC01784K
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