Citation: Wei Dai, Yuchen Liu, Tao Tong, Xingwei Li, Fang Luo. Rh(III)-catalyzed oxidative amidation of aldehydes：An efficient route to N-pyridinamides and imides[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1012-1016. doi: 10.1016/S1872-2067(14)60141-8 shu

Rh(III)-catalyzed oxidative amidation of aldehydes：An efficient route to N-pyridinamides and imides

Wei Dai ^a,, ,
Yuchen Liu ^a ,
Tao Tong ^a ,
Xingwei Li ^b ,
Fang Luo ^a,,

1.
a. College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, China;

Corresponding author: Wei Dai, Fang Luo,
Received Date: 28 March 2014
Available Online: 17 April 2014
Fund Project:

A novel Rh(III)-catalyzed direct amidation of aldehydes featuring Ag₂CO₃ as the oxidant is described. This selective procedure provides a variety of N-pyridinamides and imide derivatives in good yields.
- Rh(III)-catalyzed amidation,
- Oxidative amidation,
- Aldehyde,
- N-pyridinamide,
- Imide
1. [1]
  [1] Fraxedas J, Molecular Organic Materials: From Molecules to Crystalline Solids. Cambridge: Cambridge Univer Press, 2008
2. [2]
  [2] Bode J W. Curr Opin Drug Discovery Dev, 2006, 9: 765
3. [3]
  [3] Cupido T, Tulla-Puche J, Spengler J, Albericio F. Curr Opin Drug Discovery Dev, 2007, 10: 768
4. [4]
  [4] Pandey J, Sharma A, Tiwari V K, Dube D, Ramachandran R, Cha-turvedi V, Sinha S, Mishra N N, Shukla P K, Tripathi R P J. Comb Chem, 2009, 11: 422
5. [5]
  [5] Sheng G Z, Zhang W. Chin J Org Chem (盛国柱, 张炜. 有机化学), 2013, 33: 2271
6. [6]
  [6] Yang M, Li M, Zheng H J, Li X J. Chin J Catal (杨敏, 李敏, 郑宏杰, 李贤均. 催化学报), 2005, 26: 175
7. [7]
  [7] Hu J J, Zuo X J, Huang H M. Chin J Catal (胡金金, 左秀锦, 黄汉民. 催化学报), 2013, 34: 1644
8. [8]
  [8] Montalbetti C A G N, Falque V. Tetrahedron, 2005, 61: 10827
9. [9]
  [9] Valeur E, Bradley M. Chem Soc Rev, 2009, 38: 606
10. [10]
  [10] Bray B L. Nat Rev Drug Discovery, 2003, 2: 587
11. [11]
  [11] Albericio F. Curr Opin Chem Biol, 2004, 8: 211
12. [12]
  [12] Xiao F H, Liu Y, Tang C L, Deng G J. Org Lett, 2012, 14: 984
13. [13]
  [13] Ghosh S C, Ngiam J S Y, Seayad A M, Tuan D T, Chai C L L, Chen A Q. J Org Chem, 2012, 77: 8007
14. [14]
  [14] Kuwano S, Harada S, Oriez R, Yamada K. Chem Commun, 2012, 48: 145
15. [15]
  [15] Zhang B, Feng P, Cui Y X, Jiao N. Chem Commun, 2012, 48: 7280
16. [16]
  [16] Ghosh S C, Ngiam J S Y, Chai C L L, Seayad A M, Dang T T, Chen A Q. Adv Synth Catal, 2012, 354: 1407
17. [17]
  [17] Fu Z Q, Lee J, Kang B, Hong S H. Org Lett, 2012, 14: 6028
18. [18]
  [18] Malineni J, Merkens C, Keul H, Möller M. Catal Commun, 2013, 40: 80
19. [19]
  [19] Li H M, Xie J, Xue Q C, Cheng Y X, Zhu C J. Tetrahedron Lett, 2012, 53: 6479
20. [20]
  [20] Kazuya K, Hiroaki K, Takamichi O, Noritaka M. Angew Chem Int Ed, 2012, 51: 544
21. [21]
  [21] Gaspa S, Porcheddu A, De Luca L. Org Biomol Chem, 2013, 11: 3803
22. [22]
  [22] Kulkarni S S, Hu X D, Manetsch R. Chem Commun, 2013, 49: 1193
23. [23]
  [23] Carbone G, Burnley J, Moses J E. Chem Commun, 2013, 49: 2759
24. [24]
  [24] Zhou B, Yang Y X, Shi J J, Feng H J, Li Y C. Chem-Eur J, 2013, 19: 10511
25. [25]
  [25] Ekoue-Kovi K, Wolf C. Chem-Eur J, 2008, 14: 6302
26. [26]
  [26] De Sarkar S, Studer A. Org Lett, 2010, 12: 1992
27. [27]
  [27] Liang J, Lü J, Shang Z C. Tetrahedron, 2011, 67: 8532
28. [28]
  [28] Prasad V, Kale R R, Mishra B B, Kumar D, Tiwari V K. Org Lett, 2012, 14: 2936
29. [29]
  [29] Muthaiah S, Ghosh S C, Jee J E, Chen C, Zhang J, Hong S H. J Org Chem, 2010, 75: 3002
30. [30]
  [30] Li G L, Kung K K Y, Wong M K. Chem Commun, 2012, 48: 4112
31. [31]
  [31] Li Y M, Jia F, Li Z P. Chem-Eur J, 2013, 19: 82
32. [32]
  [32] Tillack A, Rudloff I, Beller M. Eur J Org Chem, 2001: 523
33. [33]
  [33] Chan J, Baucom K D, Murry J A. J Am Chem Soc, 2007, 129: 14106
34. [34]
  [34] Raoufmoghaddam S, Drent E, Bouwman E. Adv Synth Catal, 2013, 355: 717
35. [35]
  [35] Hiroshi F, Yoshiyuki O, Kazuya Y, Noritaka M. Angew Chem Int Ed, 2007, 46: 5202
36. [36]
  [36] Rodríguez-Lugo R E, Trincado M, Grützmacher H. ChemCatChem, 2013, 5: 1079
37. [37]
  [37] Xu L, Li N N, Peng H G, Wu P. ChemCatChem, 2013, 5: 2462
38. [38]
  [38] Zhou B, Du J J, Yang Y X, Li Y C. Org Lett, 2013, 15: 2934
39. [39]
  [39] Ng K H, Zhou Z Y, Yu W Y. Org Lett, 2012, 14: 272
40. [40]
  [40] Grohmann C, Wang H G, Glorius F. Org Lett, 2012, 14: 656
41. [41]
  [41] Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
42. [42]
  [42] Zhen W C, Du Z Y, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
43. [43]
  [43] Zhen W C, Wang F, Zhao M, Du Z Y, Li X W. Angew Chem Int Ed, 2012, 51: 11819
44. [44]
  [44] Heitman L H, van Veldhoven J P D, Zweemer A M, Ye K, Brussee J, Ijzerman A P. J Med Chem, 2008, 51: 4724
45. [45]
  [45] Kulkarni S S, Nightingale B, Dersch C M, Rothman R B, Newman A H. Bioorg Med Chem Lett, 2006, 16: 3371
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