A mild CuI-catalyzed Glaser-type homo-coupling reaction using α,α-dibromo-β-dicarbonyl compounds as oxidants

Tetrahedron

Volumn 70, Issue 2, 2014, Pages 256-261

  Fan, Xiaohui ^a,b   Li, Na ^a   Shen, Tong ^a   Cui, Xiao Meng ^a   Lv, Hao ^a   Zhu, Hong Bo ^a   Guan, Yong Hong ^a  

^a LANZHOU JIAOTONG UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

, Dibromo dicarbonyl compound; 1,3 Diyne; Copper; Coupling reaction; Glaser reaction

Indexed keywords

ALPHA,ALPHA DIBROMO BETA DICARBONYL DERIVATIVE; CARBONYL DERIVATIVE; CUPROUS ION; OXIDIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLASER TYPE HOMO COUPLING REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS;

EID: 84890792871     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.11.076     Document Type: Article

References (95)

1. F. Diederich, P.J. Stang, and R.R. Tykwinski Acetylene Chemistry: Chemistry, Biology and Material Science 2005 Wiley-VCH GmbH KGaA Weinheim, Germany
2. H.A. Stefani, A.S. Guarezemini, and R. Cella Tetrahedron 66 2010 7871
3. U.H.F. Bunz Chem. Rev. 100 2000 1605
4. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem., Int. Ed. 39 2000 2632
5. J.M. Tour Acc. Chem. Res. 33 2000 791
6. F. Bohlmann, T. Burkhardt, and C. Zdero Naturally Occurring Acetylenes 1973 Academic New York, NY
7. A.L.K. Shi Shun, and R.R. Tykwinski Angew. Chem., Int. Ed. 45 2006 1034
8. H. Yun, T.-C. Chou, H. Dong, Y. Tian, Y.-M. Li, and S.J. Danishefsky J. Org. Chem. 70 2005 10375
9. S.F. Mayer, A. Steinreiber, R.V.A. Orru, and K. Faber J. Org. Chem. 67 2002 9115
10. A.S. Ratnayake, and T. Hemscheidt Org. Lett. 4 2002 4667
11. A. Stütz Angew. Chem., Int. Ed. Engl. 26 1987 320
12. F. Babudri, D. Colangiuli, P.A. Di Lorenzo, G.M. Farinola, O.H. Omar, and F. Naso Chem. Commun. 2003 130
13. R.E. Martin, and F. Diederich Angew. Chem., Int. Ed. 38 1999 1350
14. J.M. Tour Chem. Rev. 96 1996 537
15. B.J. Morgan, X. Xie, P.-W. Phuan, and M.C. Kozlowski J. Org. Chem. 72 2007 6171
16. M. Gholami, and R.R. Tykwinski Chem. Rev. 106 2006 4997
17. M.M. Haley, and R.R. Tykwinski Carbon-rich Compounds: From Molecules to Materials 2006 Wiley-VCH GmbH KGaA Weinheim, Germany
18. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422
19. C. Glaser Ann. Chem. Pharm. 154 1870 137
20. A.S. Hay J. Org. Chem. 25 1960 1275
21. A.S. Hay J. Org. Chem. 27 1962 3320
22. G. Eglinton, and A.R. Galbraith Chem. Ind. 1956 737
23. R. Rossi, A. Carpita, and C. Bigelli Tetrahedron Lett. 26 1985 523
24. A.-W. Lei, M. Srivastava, and X.-M. Zhang J. Org. Chem. 67 2002 1969
25. X.-J. Feng, Y.-J. Ma, M. Bao, Z.-R. Zhao, F. Yang, and T.-N. Jin J. Organomet. Chem. 696 2011 1479
26. S. Perrone, F. Bona, and L. Troisi Tetrahedron 67 2011 7386
27. F. Yang, X.-L. Cui, Y.-N. Li, J.-L. Zhang, G.-R. Ren, and Y.-J. Wu Tetrahedron 63 2007 1963
28. M. Shi, and H.-X. Qian Appl. Organomet. Chem. 20 2006 771
29. J.-H. Li, Y. Liang, and X.-D. Zhang Tetrahedron 61 2005 1903
30. J. Gil-Molto, and C. Najera Eur. J. Org. Chem. 2005 4073
31. C.H. Oh, and V.R. Reddy Tetrahedron Lett. 45 2004 5221
32. E. Shirakawa, Y. Nakao, Y. Murota, and T. Hiyama J. Organomet. Chem. 670 2003 132
33. M. Qian, and E. Negishi Org. Process Res. Dev. 7 2003 412
34. Y. Liao, R. Fathi, and Z. Yang Org. Lett. 5 2003 909
35. S.V. Damle, D. Seomoon, and P.H. Lee J. Org. Chem. 68 2003 7085
36. I.J.S. Fairlamb, P.S. Bäuerlein, L.R. Marrison, and J.M. Dickinson Chem. Commun. 2003 632
37. J.D. Crowley, S.M. Goldup, N.D. Gowans, D.A. Leigh, V.E. Ronaldson, and A.M.Z. Slawin J. Am. Chem. Soc. 132 2010 6243
38. E.H. Smith, and J. Whittall Organometallics 13 1994 5169
39. K. Yin, C.-j. Li, J. Li, and X. Jia Appl. Organomet. Chem. 25 2011 16
40. Q.-W. Zheng, R.-M. Hua, and Y.-Z. Wan Appl. Organomet. Chem. 24 2010 314
41. S. Adimurthy, C.C. Malakar, and U. Beifuss J. Org. Chem. 74 2009 5648
42. P. Kuhn, P. Pale, J. Sommer, and B. Louis J. Phys. Chem. C 113 2009 2903
43. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, and N. Mizuno Angew. Chem., Int. Ed. 47 2008 2407
44. B. Alcaide, P. Almendros, R. Carrascosa, and R. Rodríguez-Acebes Eur. J. Org. Chem. 2008 1575
45. D.-F. Li, K. Yin, J. Li, and X. Jia Tetrahedron Lett. 49 2008 5918
46. B.C. Ranu, and S. Banerjee Lett. Org. Chem. 3 2006 607
47. G. Hilt, C. Hengst, and M. Arndt Synthesis 2009 395
48. C. González-Arellano, A. Abad, A. Corma, H. García, M. Iglesias, and F. Sánchez Angew. Chem., Int. Ed. 46 2007 1536
49. T.-M. Wu, S.-H. Huang, and F.-Y. Tsai Appl. Organomet. Chem. 25 2011 395
50. P. Kuhn, A. Alix, M. Kumarraja, B. Louis, P. Pale, and J. Sommer Eur. J. Org. Chem. 2009 423
51. J.S. Yadav, B.V.S. Reddy, K.B. Reddy, K.U. Gayathri, and A.R. Prasad Tetrahedron Lett. 44 2003 6493
52. J.-H. Li, and H.-F. Jiang Chem. Commun. 1999 2369
53. Y. Liu, C. Wang, X. Wang, and J.-P. Wan Tetrahedron Lett. 54 2013 3953
54. S.-L. Zhang, X.-Y. Liu, and T.-Q. Wang Adv. Synth. Catal. 353 2011 1463
55. X. Niu, C. Li, J. Li, and X. Jia Tetrahedron Lett. 53 2012 5559
56. K. Yin, C.J. Li, J. Li, and X. Jia Green. Chem. 13 2011 591
57. X. Jia, K. Yin, C.J. Li, J. Li, and H.S. Bian Green. Chem. 13 2011 2175
58. Z. Ma, X. Wang, S. Wei, H. Yang, F. Zhang, P. Wang, M. Xie, and J. Ma Catal. Commun. 39 2013 24
59. F. Nadora, M.A. Volpeb, F. Alonsoc, A. Feldhoffd, A. Kirschninge, and G. Radivoya Appl. Catal. A Gen. 455 2013 39
60. H. Li, M. Yang, X. Zhang, L. Yan, J. Li, and Y. Qi New J. Chem. 37 2013 1343
61. J.M. Pérez, R. Cano, M. Yus, and D.J. Ramón Synthesis 45 2013 1373 and references therein
62. R. Xiao, R. Yao, and M. Cai Eur. J. Org. Chem. 2012 4178
63. T. Oishi, K. Yamaguchi, and N. Mizuno ACS Catal. 1 2011 1351
64. F. Alonso, T. Melkonian, Y. Moglie, and M. Yus Eur. J. Org. Chem. 2011 2524
65. D. Wang, J. Li, N. Li, T. Gao, S. Hou, and B. Chen Green. Chem. 12 2010 45
66. K. Daisuke, K. Katsuaki, M. Tsukasa, H. Tsunehisa, and A. Shuki Tetrahedron 65 2009 10390
67. J. Yoshida, S. Yano, T. Ozawa, and N. Kawabata J. Org. Chem. 50 1985 3467
68. Using α,α-dibromo-β-dicarbonyl compounds as bromine agents in the Appel reaction has been achieved in our group. X.-M. Cui Tetrahedron Lett. 52 2013 10.1016/j.tetlet.2013.10.120
69. S.-N. Chen, W.-Y. Wu, and F.-Y. Tsai Green. Chem. 11 2009 269
70. L.-J. Li, J.-X. Wang, G.-S. Zhang, and Q.-F. Liu Tetrahedron Lett. 50 2009 4033
71. W.A. Chalifoux, M.J. Ferguson, and R.R. Tykwinski Eur. J. Org. Chem. 2007 1001
72. T. Matsuda, S. Kadowaki, and M. Murakami Chem. Commun. 2007 2627
73. K.M. Hossain, T. Shibata, and K. Takagi Synlett 2000 1137
74. Q. Liu, and D.J. Burton Tetrahedron Lett. 38 1997 4371
75. M. Vlassa, I. Ciocan-Tarta, F. Märgineanu, and I. Oprean Tetrahedron 52 1996 1337
76. J.-H. Li, Y. Liang, and Y.-X. Xie J. Org. Chem. 70 2005 4393
77. 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.C. Ward, and J. Zhu J. Org. Chem. 70 2005 703
78. F. Nador, L. Fortunato, Y. Moglie, C. Vitale, and G. Radivoy Synthesis 23 2009 4027
79. T. Oishi, T. Katayama, K. Yamaguchi, and N. Mizuno Chem. - Eur. J. 15 2009 7539
80. E. Valenti, M.A. Pericas, and F. Serratosa J. Am. Chem. Soc. 112 1990 7405
81. W.-Y. Yin, C. He, M. Chen, H. Zhang, and A.-W. Lei Org. Lett. 11 2009 709 and reference therein
82. Y.-B. Li, X.-H. Liu, H.-F. Jiang, and Z.-N. Feng Angew. Chem., Int. Ed. 49 2010 3338
83. W. Shi, Y.-D. Luo, X.-C. Luo, L. Chao, H. Zhang, J. Wang, and A.-W. Lei J. Am. Chem. Soc. 130 2008 14713
84. S. Kim, S. Kim, T. Lee, H. Ko, and D. Kim Org. Lett. 6 2004 3601
85. Y. Nishihara, K. Ikegashira, A. Mori, and T. Hiyama Tetrahedron Lett. 39 1998 4075
86. J.M. Montierth, D.R. DeMario, M.J. Kurth, and N.E. Schore Tetrahedron 54 1998 11741
87. M. Alami, and F. Ferri Tetrahedron Lett. 37 1996 2763
88. C. Amatore, E. Blart, J.P. Genet, A. Jutand, S. Lemaire-Audoire, and M. Savignac J. Org. Chem. 60 1995 6829
89. W. Chodkiewicz, J.S. Alhuwalia, P. Cadiot, and A. Willemart Compt. Rend. 245 1957 322
90. C. He, G. Zhang, J. Ke, H. Zhang, J.T. Miller, A.J. Kropf, and A. Lei J. Am. Chem. Soc. 135 2013 488
91. F. Monnier, F. Turtaut, L. Duroure, and M. Taillefer Org. Lett. 10 2008 3203
92. B.M. Trost, and M.T. Rudd J. Am. Chem. Soc. 127 2005 4763
93. S. Lysenko, J. Volbeda, P.G. Jones, and M. Tamm Angew. Chem., Int. Ed. 51 2012 6757
94. Z.-W. Chen, H.-F. Jiang, A.-Z. Wang, and S.-R. Yang J. Org. Chem. 75 2010 6700
95. C.B. Ziegler, S.M. Harris, and J.E. Baldwin J. Org. Chem. 52 1987 443