Synthesis of 1,4-diarylsubstituted 1,3-diynes through ligand-free copper-catalyzed oxidative decarboxylative homocoupling of aryl propiolic acids

Tetrahedron

Volumn 70, Issue 14, 2014, Pages 2416-2421

  Liu, De Xian ^a   Li, Fei Long ^a   Li, Hong Xi ^a   Gao, Jun ^a   Lang, Jian Ping ^a,b  

^a SOOCHOW UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,3 Diynes; Catalysis; Copper; Decarboxylative homocoupling; Ligand free

Indexed keywords

ALKYNE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER DERIVATIVE; DIMETHYL SULFOXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPIOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; DECARBOXYLATION; OXIDATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84896099324     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.02.022     Document Type: Article

References (113)

1. G. Zeni, R.B. Panatieri, E. Lissner, P.H. Menezes, A.L. Braga, and H.A. Stefani Org. Lett. 3 2001 819
2. A.S. Ratnayake, and T. Hemscheidt Org. Lett. 4 2002 4667
3. H. Yun, and S.J. Danishefsky J. Org. Chem. 68 2003 4519
4. G.A. Kraus, J. Bae, and J. Schuster Synthesis 2005 3502
5. S.A.L.K. Shi, and R.R. Tykwinski Angew. Chem., Int. Ed. 45 2006 1034
6. F. Bohlmann, T. Burkhardt, and C. Zdero Naturally Occurring Acetylenes 1973 Academic New York, NY
7. Y. Yang, Y.F. Lu, M.C. Lu, J.M. Huang, R. Haddad, G. Xomeritakis, N.G. Liu, A.P. Malanoski, D. Sturmayr, H.Y. Fan, D.Y. Sasaki, R.A. Assink, J.A. Shelnutt, F. van Swol, G.P. Lopez, A.R. Burns, and C.J. Brinker J. Am. Chem. Soc. 125 2003 1269
8. T. Aida, and K. Tajima Angew. Chem., Int. Ed. 40 2001 3803
9. F. Babudri, D. Colangiuli, P.A. Di Lorenzo, G.M. Farinola, O.H. Omar, and F. Naso Chem. Commun. 2003 130
10. R.E. Martin, and F. Diederich Angew. Chem., Int. Ed. 38 1999 1350
11. J.M. Tour Chem. Rev. 96 1996 537
12. A.D. Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M.J. Cooney, and L.T. Scott Chem. - Eur. J. 1 1995 124
13. L. Hansen, and P.M. Boll Phytochemistry 25 1986 285
14. H. Matsunaga, M. Katano, H. Yamamoto, H. Fujito, M. Mori, and K. Takata Chem. Pharm. Bull. 38 1990 3480
15. A. Stütz Angew. Chem., Int. Ed. Engl. 26 1987 320
16. M.L. Lerch, M.K. Harper, and D.J. Faulkner J. Nat. Prod. 66 2003 667
17. D. Lechner, M. Stavri, M. Oluwatuyi, R. PerdaMiranda, and S. Gibbons Phytochemistry 65 2004 331
18. C.P. Constable, and G.H.N. Towers Planta Med. 55 1989 35
19. Y.Z. Zhou, H.Y. Ma, H. Chen, L. Qiao, Y. Yao, J.Q. Cao, and Y.H. Pei Chem. Pharm. Bull. 54 2006 1455
20. M. Ladika, T.E. Fisk, W.W. Wu, and S.D. Jons J. Am. Chem. Soc. 116 1994 12093
21. S.F. Mayer, A. Steinreiber, R.V.A. Orru, and K. Faber J. Org. Chem. 67 2002 9115
22. H.L. Li, L.L. Wang, M. Yang, and Y.X. Qi Catal. Commun. 17 2012 179
23. S.H. Wang, L. Yu, P.H. Li, L.G. Meng, and L. Wang Synthesis 2011 1541
24. H.F. Jiang, and A.Z. Wang Synthesis 2007 1649
25. M. Alami, and F. Ferri Tetrahedron Lett. 37 1996 2763
26. D. Saha, T. Chatterjee, M. Mukherjee, and B.C. Ranu J. Org. Chem. 77 2012 9379
27. X.J. Feng, Z.R. Zhao, F. Yang, T.N. Jin, Y.J. Ma, and M. Bao J. Organomet. Chem. 696 2011 1479
28. S.N. Chen, W.Y. Wu, and F.Y. Tsai Green Chem. 11 2009 269
29. J.H. Li, Y. Liang, and X.D. Zhang Tetrahedron 61 2005 1903
30. I.J.S. Fairlamb, P.S. Bäuerlein, L.R. Marrison, and J.M. Dickinson Chem. Commun. 2003 632
31. T. Kurita, M. Abe, T. Maegawa, Y. Monguchi, and H. Sajiki Synlett 2007 2521
32. Q.B. Liu, and D. Burton Tetrahedron Lett. 38 1997 4371
33. A.W. Lei, M. Srivastava, and X.M. Zhang J. Org. Chem. 67 2002 1969
34. R. Rossi, A. Carpita, and C. Bigelli Tetrahedron Lett. 26 1985 523
35. F. Yang, X.L. Cui, Y.N. Li, J.L. Zhang, G.R. Ren, and Y.J. Wu Tetrahedron 63 2007 1963
36. T.M. Wu, S.H. Huang, and F.Y. Tsai Appl. Organomet. Chem. 25 2011 395
37. Y. He, and C. Cai Catal. Sci. Technol. 2 2012 1126
38. H.L. Li, M. Yang, X. Zhang, L. Yan, J. Li, and Y.X. Qi New J. Chem. 37 2013 1343
39. F. Alonso, and M. Yus ACS Catal. 2 2012 1441
40. K. Yin, C.J. Li, J. Li, and X.S. Jia Appl. Organomet. Chem. 25 2011 16
41. S.L. Zhang, X.Y. Liu, and T.Q. Wang Adv. Synth. Catal. 353 2011 1463
42. X.J. Niu, C.J. Li, J. Li, and X.S. Jia Tetrahedron Lett. 53 2012 5559
43. X.S. Jia, K. Yin, C.J. Li, J. Li, and H.S. Bian Green Chem. 13 2011 2175
44. D. Wang, J.H. Li, N. Li, T.T. Gao, S.H. Hou, and B.H. Chen Green Chem. 12 2010 45
45. D.F. Li, K. Yin, J. Li, and X.S. Jia Tetrahedron Lett. 49 2008 5918
46. K. Yin, C.J. Li, J. Li, and X.S. Jia Green Chem. 13 2011 591
47. R.A. Xiao, R.Y. Yao, and M.Z. Cai Eur. J. Org. Chem. 2012 4178
48. E.H. Smith, and J. Whittall Organometallics 13 1994 5169
49. W.Y. Yin, C. He, M. Chen, H. Zhang, and A.W. Lei Org. Lett. 11 2009 709
50. K. Fang, M.H. Xie, Z.N. Zhang, P. Ning, and G.Y. Shu Tetrahedron Lett. 54 2013 3819
51. G. Hilt, C. Hengst, and M. Arndt Synthesis 2009 395
52. X. Meng, C.B. Li, B.C. Han, T.S. Wang, and B.H. Chen Tetrahedron 66 2010 4029
53. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422
54. S.M. Bonesi, M. Fagnoni, and A. Albini Angew. Chem., Int. Ed. 47 2008 10022
55. 3 bond formation
56. R. Shang, Y. Fu, Y. Wang, Q. Xu, H. Yu, and L. Liu Angew. Chem., Int. Ed. 48 2009 9350
57. H.P. Bi, W.W. Chen, Y.M. Liang, and C.J. Li Org. Lett. 11 2009 3246
58. H.P. Bi, L. Zhao, Y.M. Liang, and C.J. Li Angew. Chem., Int. Ed. 48 2009 792
59. J. Zhou, G. Wu, M. Zhang, X.M. Jie, and W.P. Su Chem. - Eur. J. 18 2012 8032
60. 3 bond formation
61. 2 bond formation
62. J. Moon, M. Jang, and S. Lee J. Org. Chem. 74 2009 1403
63. J. Moon, M. Jeong, H. Nam, J. Ju, J.H. Moon, H.M. Jung, and S. Lee Org. Lett. 10 2008 945
64. 2 bond formation
65. L.J. GooSen, B. Zimmermann, and T. Knauber Angew. Chem., Int. Ed. 47 2008 7103
66. L.J. GooSen, F. Rudolphi, C. Oppel, and N. Rodríguez Angew. Chem., Int. Ed. 47 2008 3043
67. L.J. Goossen, N. Rodríguez, and C. Linder J. Am. Chem. Soc. 130 2008 15248
68. P. Hu, Y.P. Shang, and W.P. Su Angew. Chem., Int. Ed. 51 2012 5945
69. P. Hu, M. Zhang, X.M. Jie, and W.P. Su Angew. Chem., Int. Ed. 51 2012 227
70. J. Zhou, P. Hu, M. Zhang, S.J. Huang, M. Wang, and W.P. Su Chem. - Eur. J. 16 2010 5876
71. P. Hu, J. Kan, W.P. Su, and M.C. Hong Org. Lett. 11 2009 2341
72. H.Q. Zhao, Y. Wei, J. Xu, J. Kan, W.P. Su, and M.C. Hong J. Org. Chem. 76 2011 882
73. E.C. Burger, and J.A. Tunge Org. Lett. 6 2004 4113
74. B.M. Trost, and J. Xu J. Am. Chem. Soc. 127 2005 17180
75. M. Nakamura, A. Hajra, K. Endo, and E. Naka-mura Angew. Chem., Int. Ed. 44 2005 7248
76. L.J. Goossen, G. Deng, and L.M. Levy Science 313 2006 662
77. S. You, and L. Dai Angew. Chem., Int. Ed. 45 2006 5246
78. S.R. Waetzig, and J.A. Tunge J. Am. Chem. Soc. 129 2007 4138
79. L.J. Goossen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, and L.M. Levy J. Am. Chem. Soc. 129 2007 4824
80. B. Olivier Angew. Chem., Int. Ed. 46 2007 1373
81. J.M. Becht, C. Catala, C. LeDrian, and A. Wagner Org. Lett. 9 2007 1781
82. L.J. Goossen, and B. Melzer J. Org. Chem. 72 2007 7473
83. M. Miyasaki, A. Fukushima, T. Satoh, K. Hirano, and M. Miura Chem. - Eur. J. 15 2009 3674
84. H. Kim, and P.H. Lee Adv. Synth. Catal. 351 2009 2827
85. T.Y. Li, P. Sun, H.L. Yang, Y. Zhu, H. Yan, L.H. Lu, and J.C. Mao Tetrahedron 68 2012 6413
86. L.L. Shi, W. Jia, X. Li, and N. Jiao Tetrahedron Lett. 54 2013 1951
87. D.L. Pan, C. Zhang, S.T. Ding, and N. Jiao Eur. J. Org. Chem. 2011 4751
88. D.B. Zhao, C. Gao, X.Y. Su, Y.Q. He, J.S. You, and Y. Xue Chem. Commun. 2010 9049
89. X.M. Qu, T.Y. Li, P. Sun, Y. Zhu, H.L. Yang, and J.C. Mao Org. Biomol. Chem. 9 2011 6938
90. L. Yu, P.H. Li, and L. Wang Chem. Commun. 2013 2368
91. H.D. Feng, D.S. Ermolat'ev, G.H. Song, and E.V. Van der Eycken J. Org. Chem. 77 2012 5149
92. H.D. Feng, D.S. Ermolat'ev, G.H. Song, and E.V. Van der Eycken Adv. Synth. Catal. 354 2012 505
93. Y. Zhang, S. Patel, and N. Mainolfi Chem. Sci. 3 2012 3196
94. S. Ranjit, Z.Y. Duan, P.F. Zhang, and X.G. Liu Org. Lett. 12 2010 4143
95. Z. Huang, R. Shang, Z.R. Zhang, X.D. Tan, X. Xiao, and Y. Fu J. Org. Chem. 78 2013 4551
96. T. Palani, K. Park, M.R. Kumar, H.M. Jun, and S. Lee Eur. J. Org. Chem. 2012 5038
97. M. Yu, D. Pan, W. Jia, W. Chen, and N. Jiao Tetrahedron Lett. 51 2010 1287
98. J. Park, E. Park, A. Kim, S.A. Park, Y. Lee, K.W. Chi, Y.H. Jung, and I.S. Kim J. Org. Chem. 76 2011 2214
99. Y. Kim, A. Park, K. Park, and S. Lee Tetrahedron Lett. 52 2011 1766
100. A. Kolarovič, and Z. Fáberová J. Org. Chem. 74 2009 7199
101. A. Kolarovič, M. Schnürch, and M.D. Mihovilovic J. Org. Chem. 76 2011 2613
102. D.E. Mendes, and A.M. Schoffstall J. Chem. Educ. 88 2011 1582
103. A.S. Batsanov, J.C. Collings, I.J.S. Fairlamb, J.P. Holland, J.A.K. Howard, Z. Lin, T.B. Marder, A.C. Parsons, R.M. Ward, and J. Zhu J. Org. Chem. 70 2005 703
104. S. Adimurthy, C.C. Malakar, and U. Beifuss J. Org. Chem. 74 2009 5648
105. W. Jia, and N. Jiao Org. Lett. 12 2010 2000
106. Z.W. Chen, H.F. Jiang, A.Z. Wang, and S.R. Yang J. Org. Chem. 75 2010 6700
107. L.J. Li, J.X. Wang, G.S. Zhang, and Q.F. Liu Tetrahedron Lett. 50 2009 4033
108. Q.W. Zheng, R.M. Hua, and Y.Z. Wan Appl. Organomet. Chem. 24 2010 314
109. E. Merkul, D. Urselmann, and T.J.J. Müller Eur. J. Org. Chem. 2010 238
110. T.M. Fasina, J.C. Collings, J.M. Burke, A.,S. Batsanov, R.M. Ward, D. Albesa-Jové, L. Porrès, A. Beeby, J.A.K. Howard, A.J. Scott, W. Clegg, S.W. Watt, C. Viney, and T.B. Marder J. Mater. Chem. 15 2005 690
111. M. Arisawa, Y. Tagami, and M. Yamaguchi Tetrahedron Lett. 49 2008 1593
112. K. Park, T. Palani, A. Pyo, and S. Lee Tetrahedron Lett. 53 2012 733
113. K. Park, J.M. You, S. Jeon, and S. Lee Eur. J. Org. Chem. 2013 1973