Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen

Chemical Communications

Volumn 51, Issue 10, 2015, Pages 1823-1825

  Cao, Hua ^a   Lei, Sai ^a   Li, Naiying ^a   Chen, Longbin ^a   Liu, Jingyun ^a   Cai, Huiyin ^a   Qiu, Shuxian ^a   Tan, Jingwen ^a  

^a GUANGDONG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; OXIDIZING AGENT; OXYGEN; COPPER; DIMETHYL SULFOXIDE; IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CARBON SOURCE; CATALYST; CHEMICAL STRUCTURE; COVALENT BOND; ELECTRON TRANSPORT; FORMYLATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMISTRY; HYDROGEN BOND; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; COPPER; DIMETHYL SULFOXIDE; HYDROGEN BONDING; IMIDAZOLES; OXIDATION-REDUCTION; OXYGEN; PYRIDINES;

EID: 84921530756     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc09134e     Document Type: Article

References (52)

1. (a) R. Lauchli and K. J. Shea, Org. Lett., 2006, 8, 5287-5289;
2. (b) I. Coldham, B. C. Dobson, S. R. Fletcher and A. I. Franklin, Eur. J. Org. Chem., 2007, 2676-2686;
3. (c) A. Vilsmeier and A. Haack, Ber. Dtsch. Chem. Ges., 1927, 60, 119-122;
4. (d) S. J. Seshadri, J. Sci. Ind. Res., 1973, 32, 128-149.
5. (a) K. Reimer and F. Tiemann, Ber. Dtsch. Chem. Ges., 1876, 9, 1268-1278;
6. (b) K. Reimer, Ber. Dtsch. Chem. Ges., 1876, 9, 423-424;
7. (c) H. Wynberg, Chem. Rev., 1960, 60, 169-184.
8. M. L. Bennasar, E. Zulaica, D. Sole and S. Alonso, Tetrahedron, 2007, 63, 861-866.
9. (a) D. M. Ketcha and G. W. Gribble, J. Org. Chem., 1985, 50, 5451-5457;
10. (b) A. R. Katritzky, K. Suzuki, S. K. Singh and H. Y. He, J. Org. Chem., 2003, 68, 5720-5723;
11. (c) E. Wenkert, P. D. R. Moeller, S. R. Piettre and A. T. McPhail, J. Org. Chem., 1988, 53, 3170-3178.
12. (a) W. Wu and W. Su, J. Am. Chem. Soc., 2011, 133, 11924-11927;
13. (b) L. T. Li, J. Huang, H. Y. Li, L. J. Wen, P. Wang and B. Wang, Chem. Commun., 2012, 48, 5187-5189;
14. (c) L. T. Li, H. Y. Li, L. J. Xing, L. a. Wen, P. Wang and B. Wang, Org. Biomol. Chem., 2012, 10, 9519-9522.
15. (a) X. Li, X. Gu, Y. Li and P. Li, ACS Catal., 2014, 4, 1897-1900;
16. (b) J. Chen, B. Liu, D. Liu, S. Liu and J. Cheng, Adv. Synth. Catal., 2012, 354, 2438-2442;
17. (c) L. Zhang, C. Peng, D. Zhao, Y. Wang, H. J. Fu, Q. Shen and J. X. Li, Chem. Commun., 2012, 48, 5928-5930;
18. (d) L. T. Li, H. Y. Li, L. J. Xing, L. J. Wen, P. Wang and B. Wang, Org. Biomol. Chem., 2012, 10, 9519-9522;
19. (e) D. Zhao, Y. Wang, M. X. Zhu, Q. Shen, L. Zhang, Y. Du and J. X. Li, RSC Adv., 2013, 3, 10272-10276.
20. (a) S. Ding and N. Jiao, J. Am. Chem. Soc., 2011, 133, 12374-12377;
21. (b) Y. Q. Zou, W. Guo, F. L. Liu, L. Q. Lu, J. R. Chen and W. Xiao, Green Chem., 2014, 16, 3787-3795.
22. (a) S. Chiba, Y. F. Wang and F. L. Zhang, Synthesis, 2012, 1526-1534;
23. (b) Z. Zhang, Q. Tian, J. Qian, Q. Liu, T. Liu, L. Shi and G. Zhang, J. Org. Chem., 2014, 79, 8182-8188;
24. (c) H. Fei, J. Yu, Y. Jiang, H. Guo and J. Cheng, Org. Biomol. Chem., 2013, 11, 7092-7095;
25. (d) T. Kawakami and H. Suzuki, Tetrahedron Lett., 2000, 41, 7093-7096;
26. (e) X. Cui, Y. Zhang, Y. Deng and F. Shi, Chem. Commun., 2014, 50, 189-191;
27. (f) Y. Lv, Y. Li, T. Xiong, W. Pu, H. Zhang, K. Sun, Q. Liu and Q. Zhang, Chem. Commun., 2013, 49, 6439-6441.
28. J. Qian, Z. Zhang, Q. Liu, T. Liu and G. Zhang, Adv. Synth. Catal., 2014, 356, 3119-3124.
29. D. J. Keddie, T. E. Johnson, D. P. Arnold and S. E. Bottle, Org. Biomol. Chem., 2005, 3, 2593-2598.
30. (a) C. Dai, Z. Xu, F. Huang, Z. Yu and Y. F. Gao, J. Org. Chem., 2012, 77, 4414-4419;
31. (b) S. M. Patil, S. Kulkarni, M. Mascarenhas, R. Sharma, S. M. Roopan and A. Roychowdhury, Tetrahedron, 2013, 69, 8255-8262;
32. (c) F. Luo, C. Pan, L. Li, F. Chen and J. Cheng, Chem. Commun., 2011, 47, 5304-5306;
33. (d) L. Chu, X. Yue and F. L. Qing, Org. Lett., 2010, 12, 1644-1647.
34. G. Yuan, J. Zheng, X. Gao, X. Li, L. Huang, H. Chen and H. Jiang, Chem. Commun., 2012, 48, 7513-7515.
35. X. Ren, J. Chen, F. Chen and J. Cheng, Chem. Commun., 2011, 47, 6725-6727.
36. (a) H. Cao, H. Y. Zhan, Y. G. Lin, X. L. Lin, Z. D. Du and H. F. Jiang, Org. Lett., 2012, 14, 1688-1691;
37. (b) H. Cao, Y. G. Lin, H. Y. Zhan, Z. D. Du, X. L. Lin, Q. M. Liang and H. Zhang, RSC Adv., 2012, 2, 5972-5975;
38. (c) L. Zhao, H. Zhan, J. Liao, J. Huang, Q. Chen, H. Qiu and H. Cao, Catal. Commun., 2014, 56, 65-67;
39. (d) H. Zhan, L. Zhao, N. Li, L. Chen, J. Liu, J. Liao and H. Cao, RSC Adv., 2014, 4, 32013-32016.
40. H. Cao, X. H. Liu, L. Zhao, J. H. Cen, J. X. Lin, Q. X. Zhu and M. L. Fu, Org. Lett., 2014, 16, 146-149.
41. (a) C. M. Marson, Chem. Soc. Rev., 2011, 40, 5514-5533;
42. (b) M. A. Ismail, R. K. Arafa, T. Wenzler, R. Brun, F. A. Tanious, W. D. Wilson and D. W. Boykin, Bioorg. Med. Chem., 2008, 16, 681-685;
43. (c) G. Puerstinger, J. Paeshuyse, E. Declercq and J. Neyts, Bioorg. Med. Chem. Lett., 2007, 17, 390-393;
44. (d) K. S. Gudmundsson and B. A. Johns, Bioorg. Med. Chem. Lett., 2007, 17, 2735-2739.
45. (a) S. Marhadour, M. A. Bazin and P. Marchand, Tetrahedron Lett., 2012, 53, 297-300;
46. (b) N. Chernyak and V. Gevorgyan, Angew. Chem., Int. Ed., 2010, 49, 2743;
47. (c) J. Zeng, Y. J. Tan, M. L. Leow and X. W. Liu, Org. Lett., 2012, 14, 4386-4389;
48. (d) S. Husinec, R. Markovic, M. Petkovic, V. Nasufovic and V. Savic, Org. Lett., 2011, 13, 2286-2289;
49. (e) Y. Gao, M. Z. Yin, W. Q. Wu, H. W. Huang and H. F. Jiang, Adv. Synth. Catal., 2013, 355, 2263-2273;
50. (f) H. W. Huang, X. C. Ji, X. D. Tang, M. Zhang, X. W. Li and H. F. Jiang, Org. Lett., 2013, 15, 6254-6257;
51. (g) H. Yang, L. Yang, Y. Li, F. Zhang, H. Liu and B. Yi, Catal. Commun., 2012, 11-14.
52. H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang and Q. Zhu, Angew. Chem., Int. Ed., 2011, 50, 5678-5681.