Diacylation of coumarins by silver-catalyzed decarboxylative cross-coupling

Tetrahedron

Volumn 71, Issue 4, 2015, Pages 630-636

  Wang, Hua ^a   Zhou, Shi Liu ^a   Guo, Li Na ^a   Duan, Xin Hua ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Acylation; Decarboxylation; Radical; Silver catalyzed; Substituted coumarins

Indexed keywords

2 BENZOYL 3,5 DIMETHYL [1,4]BENZOQUINONE; 3 (4 BROMO BENZOYL) CHROMEN 2 ONE; 3 (4 CHLORO BENZOYL) CHROMEN 2 ONE; 3 (4 FLUORO BENZOYL) CHROMEN 2 ONE; 3 (4 IODO BENZOYL) CHROMEN 2 ONE; 3 (4 METHOXY BENZOYL) CHROMEN 2 ONE; 3 (4 METHYL BENZOYL) CHROMEN 2 ONE; 3 (NAPHTHALENE 2 CARBONYL) CHROMEN 2 ONE; 3 (THIOPHENE 2 CARBONYL) CHROMEN 2 ONE; 3 BENZOYL 7 HYDROXY 4 METHYL CHROMEN 2 ONE; 3 BENZOYL CHROMEN 2 ONE; 3,4 BIS (2 CHLORO BENZOYL) CHROMEN 2 ONE; 3,4 BIS (2 FLUORO BENZOYL) CHROMEN 2 ONE; 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 3,4 BIS (2,4 DIMETHYL BENZOYL) CHROMEN 2 ONE; 3,4 BIS (4 FLUORO BENZOYL) CHROMEN 2 ONE; 3,4 BIS (4 METHOXY BENZOYL) CHROMEN 2 ONE; 3,4 BIS (4 METHYL BENZOYL) CHROMEN 2 ONE; 3,4 DIBENZOYL 1 METHYL 1H QUINOLIN 2 ONE; 3,4 DIBENZOYL CHROMEN 2 ONE; 5,8 DIMETHYL 3 (2 METHYL BENZOYL) CHROMEN 2 ONE; 6 METHYL 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 6,8 DICHLORO 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 6,8 DIMETHYL 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 7 CHLORO 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 7 METHOXY 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; 8 METHYL 3,4 BIS (2 METHYL BENZOYL) CHROMEN 2 ONE; COUMARIN DERIVATIVE; SILVER; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CROSS COUPLING REACTION; DECARBOXYLATION; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84920487073     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.12.029     Document Type: Article

References (67)

1. S. Sandhu, Y. Bansal, O. Silakari, and G. Bansal Bioorg. Med. Chem. 22 2014 3806 For recent examples, see
2. B. Li, R. Pai, M. Di, D. Aiello, M.H. Barnes, M.M. Butler, T.F. Tashjian, N.P. Peet, T.L. Bowlin, and D.T. Moir J. Med. Chem. 55 2012 10896
3. P. Anand, B. Singh, and N. Singh Bioorg. Med. Chem. 20 2012 1175
4. Q. Zou, Y. Fang, Y. Zhao, H. Zhao, Y. Wang, Y. Gu, and F. Wu J. Med. Chem. 56 2013 5288
5. A.R. Jagtap, V.S. Satam, R.N. Rajule, and V.R. Kanetkar Dyes Pigment 82 2009 84
6. C.-H. Chang, H.-C. Cheng, Y.-J. Lu, K.-C. Tien, H.-W. Lin, C.-L. Lin, C.-J. Yang, and C.-C. Wu Org. Electron. 11 2010 247
7. J.A. Joule, and K. Mills Heterocyclic Chemistry 4th ed. 2000 Blackwell Oxford, UK
8. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, and Y. Fujiwara Science 287 2000 1992
9. H.S.P. Rao, and S. Sivakumar J. Org. Chem. 71 2006 8715
10. Y. Yamamoto, and N. Kirai Org. Lett. 10 2008 5513
11. X.-F. Xia, X.-Z. Shu, K.-G. Ji, A. Shaukat, X.-Y. Liu, and Y.-M. Liang J. Org. Chem. 76 2011 342
12. D. Kim, M. Min, and S. Hong Chem. Commun. 2013 4021
13. J. Wei, P. Wang, Q. Jia, J. Huang, Z. Du, K. Zhang, and J. Wang Eur. J. Org. Chem. 2013 4499
14. X. Mi, C. Wang, M. Huang, J. Zhang, Y. Wu, and Y. Wu Org. Lett. 16 2014 3356
15. M. Khoobi, M. Alipour, S. Zarei, F. Jafarpour, and A. Shafiee Chem. Commun. 2012 2985
16. Y. Li, Z. Qi, H. Wang, X. Fu, and C. Duan J. Org. Chem. 77 2012 2053
17. M. Min, and S. Hong Chem. Commun. 2012 9613
18. M. Min, Y. Kim, and S. Hong Chem. Commun. 2013 196
19. X. Mi, M. Huang, J. Zhang, C. Wang, and Y. Wu Org. Lett. 15 2013 6266
20. F. Jafarpour, H. Hazrati, N. Mohasselyazdi, M. Khoobi, and A. Shafiee Chem. Commun. 2013 10935
21. X.-H. Cao, X. Pan, P.-J. Zhou, J.-P. Zou, and O.T. Asekun Chem. Commun. 2014 3359
22. S.-L. Zhou, L.-N. Guo, and X.-H. Duan Eur. J. Org. Chem. 2014 8094
23. D.V. Kadnikov, and R.C. Larock Org. Lett. 2 2000 3643
24. D.V. Kadnikov, and R.C. Larock J. Org. Chem. 68 2003 9423
25. L. Zhang, T. Meng, R. Fan, and J. Wu J. Org. Chem. 72 2007 7279
26. H. Sun, Y. Zhang, F. Guo, Y. Yan, C. Wan, Z. Zha, and Z. Wang Eur. J. Org. Chem. 2012 480
27. S. Kim, D. Kang, C.-H. Lee, and P.H. Lee J. Org. Chem. 77 2012 6530
28. O. Baudoin Angew. Chem., Int. Ed. 46 2007 1373
29. L.J. Goossen, N. Rodríguez, and K. Goossen Angew. Chem., Int. Ed. 47 2008 3100
30. T. Satoh, and M. Miura Synthesis 2010 3395
31. N. Rodríguez, and L.J. Goossen Chem. Soc. Rev. 40 2011 5030
32. R. Shang, and L. Liu Sci. China Chem. 54 2011 1670
33. W.I. Dzik, P.P. Lange, and L.J. Goossen Chem. Sci. 3 2012 2671
34. J. Cornella, and I. Larrosa Synthesis 2012 653
35. A.G. Myers, D. Tanaka, and M.R. Mannion J. Am. Chem. Soc. 124 2002 11250
36. L.J. Goossen, G. Deng, and L.M. Levy Science 313 2006 662
37. P. Forgione, M.-C. Brochu, M. St-Onge, K.H. Thesen, M.D. Bailey, and F. Bilodeau J. Am. Chem. Soc. 128 2006 11350
38. M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, and M. Miura Chem. - Eur. J. 15 2009 3674
39. F. Zhang, and M.F. Greaney Org. Lett. 12 2010 4745
40. J.-J. Dai, J.-H. Liu, D.-F. Luo, and L. Liu Chem. Commun. 2011 677
41. S. Messaoudi, J.-D. Brion, and M. Alami Org. Lett. 14 2012 1496
42. Y. Zhang, S. Patel, and N. Mainolfi Chem. Sci. 3 2012 3196
43. L.J. Goossen, F. Rudolphi, C. Oppel, and N. Rodríguez Angew. Chem., Int. Ed. 47 2008 3043
44. L.J. Goossen, B. Zimmermann, and T. Knauber Angew. Chem., Int. Ed. 47 2008 7103
45. P. Fang, M. Li, and H. Ge J. Am. Chem. Soc. 132 2010 11898
46. M. Li, and H. Ge Org. Lett. 12 2010 3464
47. H. Wang, L.-N. Guo, and X.-H. Duan Org. Lett. 14 2012 4358
48. Z. Yang, X. Chen, J. Liu, Q. Gui, K. Xie, M. Li, and Z. Tan Chem. Commun. 2013 1560
49. J. Park, M. Kim, S. Sharma, E. Park, A. Kim, S.H. Lee, J.H. Kwak, Y.H. Jung, and I.S. Kim Chem. Commun. 2013 1654
50. H. Li, P. Li, Q. Zhao, and L. Wang Chem. Commun. 2013 9170
51. J. Yao, R. Feng, Z. Wu, Z. Liu, and Y. Zhang Adv. Synth. Catal. 355 2013 1517
52. Z.-Y. Li, D.-D. Li, and G.-W. Wang J. Org. Chem. 78 2013 10414
53. H. Wang, L.-N. Guo, and X.-H. Duan Adv. Synth. Catal. 355 2013 2222
54. H. Yang, L.-N. Guo, and X.-H. Duan RSC Adv. 4 2014 52986
55. H. Wang, L.-N. Guo, and X.-H. Duan Chem. Commun. 2014 7382 For other related examples reported in our group, see
56. S. Zhang, L.-N. Guo, H. Wang, and X.-H. Duan Org. Biomol. Chem. 11 2013 4308
57. H. Wang, L.-N. Guo, and X.-H. Duan Org. Biomol. Chem. 11 2013 4573
58. H. Wang, H. Yang, Y. Li, and X.-H. Duan RSC Adv. 4 2014 8720
59. F. Pérez-Cruz, S. Vazquez-Rodriguez, M.J. Matos, A. Herrera-Morales, F.A. Villamena, A. Das, B. Gopalakrishnan, C. Olea-Azar, L. Santana, and E. Uriarte J. Med. Chem. 56 2013 6136
60. Y. Wang, Z.-H. Yu, H.-F. Zheng, and D.-Q. Shi Org. Biomol. Chem. 10 2012 7739
61. T.-Y. Jian, X.-Y. Chen, L.-H. Sun, and S. Ye Org. Biomol. Chem. 11 2013 158
62. J.M. Anderson, and J.K. Kochi J. Am. Chem. Soc. 92 1970 1651
63. J.M. Anderson, and J.K. Kochi J. Org. Chem. 35 1970 986
64. F. Fontana, F. Minisci, M. Claudia, N. Barbosa, and E. Vismara J. Org. Chem. 56 1991 2866
65. K. Wadhwa, C. Yang, P.R. West, K.C. Deming, S.R. Chemburkar, and R.E. Reddy Synth. Commun. 38 2008 4434
66. R.K. Verma, G.K. Verma, G. Shukla, and M.S. Singh RSC Adv. 2 2012 2413
67. N. Dnyanoba, M. Nagahama, T. Inaba, Y. Nishino, K. Miura, S. Kosaka, J. Fukao, I. Kawasaki, and S. Ohta Heterocycles 65 2005 2411