Co2(CO)8-mediated cycloisomerization of arylene 1,7-enynes

Tetrahedron Letters

Volumn 54, Issue 7, 2013, Pages 699-702

  Xing, Ping ^a   Huang, Zuo Gang ^b   Jin, Yun ^a   Jiang, Biao ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI ADVANCED RESEARCH INSTITUTE   (China)

Author keywords

1,7 Enyne; 2,3 Dihydroindene; Cycloisomerization; Dicobalt octacarbonyl

Indexed keywords

ALIPHATIC COMPOUND; AROMATIC COMPOUND; ARYLENE 1,7 ENYNE; INDENE DERIVATIVE; LEWIS BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOISOMERIZATION; ELIMINATION REACTION; ISOMERIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84872177251     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.12.016     Document Type: Article

References (83)

1. For reviews see V. Michelet, P.Y. Toullec, and J.-P. Genet Angew. Chem., Int. Ed. 47 2008 4268
2. L.-M. Zhang, J.-W. Sun, and S.A. Kozmin Adv. Synth. Catal. 348 2006 2271
3. B.M. Trost, M.U. Frederiksen, and M.T. Rudd Angew. Chem., Int. Ed. 44 2005 6630
4. G.A. Solan Organomet. Chem. 32 2005 314
5. C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
6. B.M. Trost, F.D. Toste, and A.B. Pinkerton Chem. Rev. 101 2001 2067
7. B.M. Trost Chem. Eur. J. 4 1998 2405
8. B.M. Trost, and M.J. Krische Synlett 1998 1
9. I. Ojima, M. Tzamarioudaki, Z.Y. Li, and R.J. Donovan Chem. Rev. 96 1996 635
10. For examples see C. Gryparis, C. Efe, C. Raptis, I.N. Lykakis, and M. Stratakis Org. Lett. 14 2012 2956
11. T. Ozawa, T. Kurahashi, and S. Matsubara Org. Lett. 14 2012 3008
12. W.-F. Wang, J.-M. Yang, F.-J Wang, and M. Shi Organometallics 30 2011 3859
13. E.G. Corkum, M.J. Hass, A.D. Sullivan, and S.H. Bergens Org. Lett. 13 2011 3522
14. T. Nishimura, Y. Maeda, and T. Hayashi Org. Lett. 13 2011 3674
15. V. Lopez-Carrillo, N. Huguet, A. Mosquera, and A. Echavarren Chem. Eur. J. 17 2011 10972
16. S.-Y. Kim, and Y.-K. Chung J. Org. Chem. 75 2010 1281
17. B.M. Trost, A.C. Gutierrez, and E.M. Ferreira J. Am. Chem. Soc. 132 2010 9206
18. A. Fuerstner, K. Majima, R. Martin, H. Krause, E. Kattnig, R. Goddard, and C.W. Lehmann J. Am. Chem. Soc. 2008 1992 130
19. A. Fuerstner, R. Martin, and K. Majima J. Am. Chem. Soc. 127 2005 12236
20. B. Schmidt Eur. J. Org. Chem. 9 2004 1865
21. G.C. Lloyd-Jones Org. Biomol. Chem. 1 2003 215
22. For reviews see G. Dominguez, and J. Perez-Castells Chem. Soc. Rev. 40 2011 3430
23. For examples see N. Weding, R. Jackstell, H. Jiao, A. Spannenberg, and M. Hapke Adv. Synth. Catal. 353 2011 3423
24. Y.K. Sugiyama, R. Kato, T. Sakurada, and S. Okamoto J. Am. Chem. Soc. 133 2011 9712
25. C.C. Eichman, J.P. Bragdon, and J.P. Stambuli Synlett 2011 1109
26. P. Turek, M. Hocek, R. Pohl, B. Klepetarova, and M. Kotora Eur. J. Org. Chem. 19 2008 3335
27. G. Hilt, C. Hengst, and W. Hess Eur. J. Org. Chem. 13 2008 2293
28. N. Agenet, V. Gandon, K.P.C. Vollhardt, M. Malacria, and C. Aubert J. Am. Chem. Soc. 129 2007 8860
29. H.-T. Chang, M. Jeganmohan, and C.-H. Cheng Org. Lett. 9 2007 505
30. M. Lombardo, F. Pasi, C. Trombini, K.R. Seddon, and W.R. Pitner Green Chem. 9 2007 321
31. G. Hilt, T. Vogler, W. Hess, and F. Galbiati Chem. Commun. 11 2005 1474
32. G. Hilt, W. Hess, T. Vogler, and C. Hengst J. Organomet. Chem. 690 2005 5170
33. M. Petit, C. Aubert, and M. Malacria Org. Lett. 6 2004 3937
34. N.E. Shore B.M. Trost, I. Felming, L.A. Paquette, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Press Oxford 1037 1064
35. O. Geis, and H.-G. Schmalz Angew. Chem., Int. Ed. 37 1998 911
36. S.E. Gibson, and N. Mainolfi Angew. Chem., Int. Ed. 44 2005 3022
37. X.C. Cambeiro, and M.A. Pericas R. Rios Torres, The Pauson-Khand Reaction: Scope, Variations and Applications 2012 John Wiley & Sons
38. For reviews see G. Hilt Synlett 2011 1654
39. M. Lautcns, W. Tam, J. CraigLautens, C.G. Edwards, C.M. Crudden, and C. Smith J. Am. Chem. Soc. 117 1995 6863
40. For examples see M. Arndt, G. Hilt, A.F. Khlebnikov, S.I. Kozhushkov, and A. Meijere Eur. J. Org. Chem. 16 2012 3112
41. F. Erver, and G. Hilt Org. Lett. 14 2012 1884
42. C. Reus, N.-W. Liu, M. Bolte, H.-W. Lerner, and M. Wagner J. Org. Chem. 77 2012 3518
43. F. Erver, G. Hilt, and K. Harms Synthesis 2011 972
44. G. Hilt, M. Arndt, and D.F. Weske Synthesis 2010 1321
45. G. Hilt, and J. Janikowski Org. Lett. 11 2009 773
46. P. Moerschel, J. Janikowski, G. Hilt, and G. Frenking J. Am. Chem. Soc. 130 2008 8952
47. G. Hilt, and M. Danz Synthesis 2008 225
48. G. Hilt, W. Hess, and K. Harms Org. Lett. 8 2006 3287
49. G. Hilt, J. Jaikowski, and W. Hess Angew. Chem., Int. Ed. 45 2006 5204
50. G. Hilt, S. Luers, and K. Harms J. Org. Chem. 69 2004 624
51. G. Hilt, F. Erver, and K. Harms Org. Lett. 13 2011 304
52. G. Hilt, A. Paul, and J. Treutwein Org. Lett. 12 2010 1536
53. G. Hilt, and J. Treutwein Angew. Chem., Int. Ed. 46 2007 8500
54. G.E. Hutson, A.H. Dave, and V.H. Rawal Org. Lett. 9 2007 3869
55. S. Kezuka, T. Ikeno, and T. Yamada Org. Lett. 3 2001 1937
56. D. Llerena, C. Aubert, and M. Malacria Tetrahedron Lett. 37 1996 7027
57. O. Buisine, C. Aubert, and M. Malacria Chem. Eur. J. 7 2001 3517
58. D. Llerena, C. Aubert, and M. Malacria Tetrahedron Lett. 37 1996 7353
59. A. Ajamian, and J.L. Gleason Org. Lett. 5 2003 2409
60. A. Ajamian, and J.L. Gleason Org. Lett. 3 2001 4161
61. R. Dolaine, and J.L. Gleason Org. Lett. 2 2000 1753
62. B. Jiang, and M. Xu Angew. Chem., Int. Ed. 43 2004 2543
63. B. Jiang, and M. Xu Org. Lett. 4 2002 4077
64. I.U. Khand, G.R. Knox, P.L. Pauson, and W.E. Watts J. Chem. Soc. Chem. Commun. 1 1971 36
65. P. Magnus, and L.M. Principe Tetrahedron Lett. 26 1985 4851
66. P. Magnus, C. Exon, and P. Albaugh-Robertson Tetrahedron 41 1985 5861
67. P. Magnus, L.M. Principe, and M.J. Slater J. Org. Chem. 52 1987 1483
68. K.D. Wellington, R.C. Cambie, P.S. Rutledge, and P.R. Bergquist J. Nat. Prod. 63 2000 79
69. C.M. Madu, and C.J. Lovely Org. Lett. 9 2007 4697
70. E. Arnaiz, J. Blanco-Urgoiti, D. Abdi, G. Dominguez, and J.P. Castells J. Organomet. Chem. 693 2008 2431
71. L.V.R. Bonaga, and M.E. Krafft Tetrahedron 60 2004 9795
72. For a less sterically hindered example: J. Blanco-Urgoiti, D. Abdi, G. Dominguez, and J. Perez-Castells Tetrahedron 64 2008 67
73. For less sterically hindered examples T. Morimoto, K. Fuji, K. Tsutsumi, and K. Kakiuchi J. Am. Chem. Soc. 124 2002 3806
74. K. Fuji, T. Morimoto, K. Tsutsumi, and K. Kakiuchi Angew. Chem., Int. Ed. 42 2003 2409
75. K. Ikeda, T. Morimoto, T. Tsumagari, H. Tanimoto, Y. Nishiyama, and K. Kakiuchi Synlett 2012 393
76. W.J. Kerr R. Rios Torres, The Pauson-Khand Reaction: Scope, Variations and Applications 2012 John Wiley & Sons
77. T. Shibata R. Rios Torres, The Pauson-Khand Reaction: Scope, Variations and Applications 2012 John Wiley & Sons
78. S.E. Gibson, and A. Stevenazzi Angew. Chem., Int. Ed. 2003 1800 42
79. T. Sugihara, M. Yamaguchi, and M. Nishizawa Chem. Eur. J. 7 2001 1589
80. Catalytic Pauson-Khand reaction using Lewis base as ligand. See Y.-F. Tang, L.-J. Deng, Y.-D. Zhang, G.-B. Dong, J.-H. Chen, and Z. Yang Org. Lett. 7 2005 593
81. M.E. Krafft, L.V.R. Bonaga, and C. Hirosawa J. Org. Chem. 66 2001 3004
82. M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo Angew. Chem., Int. Ed. 39 2000 631
83. N. Jeong, S.H. Hwang, Y. Lee, and Y.K. Chung J. Am. Chem. Soc. 116 1994 3159