Citation: Hao Liang, Zhihui Ren, Yaoyu Wang, Zhenghui Guan. One-pot green synthesis of enamides and 1,3-diynes[J]. Chinese Journal of Catalysis, ;2015, 36(1): 113-118. doi: 10.1016/S1872-2067(14)60220-5 shu

One-pot green synthesis of enamides and 1,3-diynes

1.
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, Shaanxi, China

Corresponding author: Zhenghui Guan,
Received Date: 19 July 2014
Available Online: 2 September 2014
Fund Project: 国家自然科学基金(21272183) (21272183) 陕西省科技厅“陕西省青年科技新星”基金(2012KJXX-26). (2012KJXX-26)

A green organic synthetic method combining reductive acylation of ketoximes and oxidative coupling of terminal alkynes was developed. This novel process enables enamides and 1,3-diynes to be synthesized simultaneously in high yields and under mild conditions without the use of terminal reductants/oxidants.
- Green synthesis,
- Ketoxime,
- Terminal alkyne,
- Enamide,
- 1,3-Diyne
1. [1]
  [1] Allen S E, Walvoord R R, Padilla-Salinas R, Kozlowski M C. Chem Rev, 2013, 113: 6234
2. [2]
  [2] Saisaha P, de Boer J W, Browne W R. Chem Soc Rev, 2013, 42: 2059
3. [3]
  [3] Wu W Q, Jiang H F. Acc Chem Res, 2012, 45: 1736
4. [4]
  [4] Campbell A N, Stahl S S. Acc Chem Res, 2012, 45: 851
5. [5]
  [5] Punniyamurthy T, Velusamy S, Iqbal J. Chem Rev, 2005, 105: 2329
6. [6]
  [6] Verendel J J, Pàmies O, Diéguez M, Andersson P G. Chem Rev, 2014, 114: 2130
7. [7]
  [7] Etayo P, Vidal-Ferran A. Chem Soc Rev, 2013, 42: 728
8. [8]
  [8] Wang D S, Chen Q A, Lu S M, Zhou Y G. Chem Rev, 2012, 122: 2557
9. [9]
  [9] Xie J H, Zhu S F, Zhou Q L. Chem Rev, 2011, 111: 1713
10. [10]
  [10] Sheldon R A, Arends I W C E, Hanefeld U. Green Chemistry and Catalysis. Weinheim: Wiley-VCH, 2007. 1
11. [11]
  [11] Caron S, Dugger R W, Ruggeri S G, Ragan J A, Ripin D H B. Chem Rev, 2006, 106: 2943
12. [12]
  [12] Burkhardt E R, Matos K. Chem Rev, 2006, 106: 2617
13. [13]
  [13] Muzart J. Chem Rev, 1992, 92: 113
14. [14]
  [14] Sheldon R A. Chem Soc Rev, 2012, 41: 1437
15. [15]
  [15] Anastas P, Eghbali N. Chem Soc Rev, 2010, 39: 301
16. [16]
  [16] Horvath I T, Anastas P T. Chem Rev, 2007, 107: 2169
17. [17]
  [17] Chen M, Ren Z H, Wang Y Y, Guan Z H. Angew Chem Int Ed, 2013, 52: 14196
18. [18]
  [18] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Chem Eur J, 2014, 20: 1839
19. [19]
  [19] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Org Lett, 2014, 16: 608
20. [20]
  [20] Zhao M N, Du W, Ren Z H, Wang Y Y, Guan Z H. Eur J Org Chem, 2013, 2013: 7989
21. [21]
  [21] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Chem Commun, 2012, 48: 8105
22. [22]
  [22] Lei C H, Wang D X, Zhao L, Zhu J P, Wang M X. J Am Chem Soc, 2013, 135: 4708
23. [23]
  [23] Pankajakshan S, Xu Y H, Cheng J K, Low M T, Loh T P. Angew Chem Int Ed, 2012, 51: 5701
24. [24]
  [24] Matsubara R, Kobayashi S. Acc Chem Res, 2008, 41: 292
25. [25]
  [25] Liang H, Ren Z H, Wang Y Y, Guan Z H, Chem Eur J, 2013, 19: 9789
26. [26]
  [26] Guan Z H, Zhang Z Y, Ren Z H, Wang Y Y, Zhang X M. J Org Chem, 2011, 76: 339
27. [27]
  [27] Tang W J, Capacci A, Sarvestani M, Wei X D, Yee N K, Senanayake C H. J Org Chem, 2009, 74: 9528
28. [28]
  [28] Zhao H, Vandenbossche C P, Koenig S G, Singh S P, Bakale R P. Org Lett, 2008, 10: 505
29. [29]
  [29] Hughes R A, Thompson S P, Alcaraz L, Moody C J. J Am Chem Soc, 2005, 127: 15644
30. [30]
  [30] Haley M M, Tykwinski R R. Carbon-Rich Compounds: From Molecules to Materials. Weinheim: Wiley-VCH, 2006. 295
31. [31]
  [31] Shun A L K S, Tykwinski R R. Angew Chem Int Ed, 2006, 45: 1034
32. [32]
  [32] Diederich F, Stang P J, Tykwinski R R. Acetylene Chemistry: Chemistry, Biology and Material Science. Weinheim: Wiley-VCH, 2005. 233
33. [33]
  [33] Shi W, Lei A W. Tetrahedron Lett, 2014, 55: 2763
34. [34]
  [34] Feng X J, Zhao Z R, Yang F, Jin T N, Ma Y J, Bao M. J Organomet Chem, 2011, 696: 1479
35. [35]
  [35] Li J H, Liang Y, Zhang X D. Tetrahedron, 2005, 61: 1903
36. [36]
  [36] Doi T, Orita A, Matsuo D, Saijo R, Otera J. Synlett, 2008: 55
37. [37]
  [37] Lei A W, Srivastava M, Zhang X M. J Org Chem, 2002, 67: 1969
38. [38]
  [38] Rossi R, Carpita A, Bigelli C. Tetrahedron Lett, 1985, 26: 523
39. [39]
  [39] Zhao M N, Liang H, Ren Z H, Guan Z H. Synthesis, 2012, 44: 1501
40. [40]
  [40] Ren Z H, Zhang Z Y, Yang B Q, Wang Y Y, Guan Z H. Org Lett, 2011, 13: 5394
41. [41]
  [41] Ran L F, Ren Z H, Wang Y Y, Guan Z H. Green Chem, 2014, 16: 112
42. [42]
  [42] Zhang C, Tang C H, Jiao N. Chem Soc Rev, 2012, 41: 3464
43. [43]
  [43] Ran L F, Liang H, Guan Z H. Chin J Org Chem (冉陇飞, 梁浩, 关正辉. 有机化学), 2013, 33: 66
44. [44]
  [44] Narasaka K, Kitamura M. Eur J Org Chem, 2005: 4505
45. [45]
  [45] Reeves J T, Tan Z L, Han Z S, Li G S, Zhang Y D, Xu Y B, Reeves D C, Gonnella N C, Ma S L, Lee H, Lu B Z, Senanayake C H. Angew Chem Int Ed, 2012, 51: 1400
46. [46]
  [46] Quiclet-Sire B, Tölle N, Zafar S N, Zard S Z. Org Lett, 2011, 13:3266
47. [47]
  [47] Shi W, Luo Y D, Luo X C, Chao L, Zhang H, Wang J, Lei A W. J Am Chem Soc, 2008, 130: 14713
48. [48]
  [48] Liu Q B, Burton D J. Tetrahedron Lett, 1997, 38: 4371
49. [49]
  [49] Cai C Z, Vasella A. Helv Chim Acta, 1995, 78: 2053
50. [50]
  [50] Alper H, Saldana-Maldonado M. Organometallics, 1989, 8: 1124
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