Sequential synthesis of furans from alkynes: Successive ruthenium(II)- and copper(II)-catalyzed processes

Angewandte Chemie - International Edition

Volumn 48, Issue 9, 2009, Pages 1681-1684

  Zhang, Min ^a,b   Jiang, Huan Feng ^b   Neumann, Helfried ^c   Beller, Matthias ^c   Dixneuf, Pierre H ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^c UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Alkynes; Copper; Dienyl ethers; Furans; Ruthenium

Indexed keywords

CATALYSIS; COPPER; COPPER COMPOUNDS; ETHERS; ORGANIC COMPOUNDS; RUTHENIUM; TOLUENE;

ALKYL ETHERS; ALKYNES; CATALYTIC REACTIONS; CHEMICAL EQUATIONS; DIENYL ETHERS; FURANS; ONE POTS; SEQUENTIAL SYNTHESIS; SULFONIC ACIDS; TERMINAL ALKYNES;

ACETYLENE;

ALKYNE; COPPER; FURAN DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; CATALYSIS; COPPER; CYCLIZATION; FURANS; RUTHENIUM;

EID: 60749102477     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805531     Document Type: Article

References (85)

1. a) D. J. Mortensen, A. L. Rodriguez, K. E. Carlson, J. Sun, B. S. Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 2001, 44, 3838;
2. b) I. Francesconi, W. D. Wilson, F. A. Tanious, J. E. Hall, B. C. Bender, R. R. Tidwell, D. McCurdy, D. W. Boykin, J. Med. Chem. 1999, 42, 2260;
3. c) S. M. Rahmathullah, J. E. Hall, B. C. Bender, D. R. McCurdy, R. R. Tidwell, D. W. Boykin, J. Med. Chem. 1999, 42, 3994.
4. L. Z. Zhang, C. W. Chen, C. F. Lee, C. C. Wu, T. Y. Luh, Chem. Commun. 2002, 233.
5. a) A. S. Dudnik, A. W. Sromek, M. Rubina, J. T. Kim, A. V. Kel'in, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 1440;
6. b) T. Schwier, A. W. Sromek, D. M. L. Yap, D. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 9868;
7. c) L. L. Peng, X. Zhang, M. Ma, J. B. Wang, Angew. Chem. 2007, 119, 1937;
8. Angew. Chem. Int. Ed. 2007, 46, 1905;
9. d) A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 10500;
10. e) Y. Z. Xia, A. S. Dudnik, V. Gevorgyan, Y. H. Li, J. Am. Chem. Soc. 2008, 130, 6940;
11. f) A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2007, 119, 5287;
12. Angew. Chem. Int. Ed. 2007, 46, 5195.
13. a) J. Roger, H. Doucet, Org. Biomol. Chem. 2008, 6, 169;
14. b) L. B. Zhao, Z. H. Guan, Y. X. Xie, S. He, Y. M. Liang, J. Org. Chem. 2007, 72, 10276;
15. c) B. Lu, B. Wang, Y. H. Zhang, D. W. Ma, J. Org. Chem. 2007, 72, 5337;
16. d) Y. J. Xiao, J. L. Zhang, Angew. Chem. 2008, 120, 1929;
17. Angew. Chem. Int. Ed. 2008, 47, 1903;
18. e) A. S. Karpov, E. Merkul, T. Oeser, T. J. J. Müller, Eur. J. Org. Chem. 2006, 2991;
19. f) J. L. Zhang, H. G. Schmalz, Angew. Chem. 2006, 118, 6856;
20. Angew. Chem. Int. Ed. 2006, 45, 6704.
21. a) "Metal-Catalyzed Cascade Reactions (Ed.: T. J. J. Müller)": Top. Organomet. Chem. 2006, 19;
22. b) D. E. Fogg, E. N. Santos, Coord. Chem. Rev. 2004, 248, 2365;
23. c) C. Bruneau, P. H. Dixneuf, Top. Organomet. Chem. 2004, 11, 1-44;
24. d) M. Zhang, H. F. Jiang, H. L. Liu, Q. H. Zhu, Org. Lett. 2007, 9, 4111;
25. e) M. Zhang, H. F. Jiang, Eur. J. Org. Chem. 2008, 3519;
26. f) H. Lebel, C. Ladjel, L. Brethous, J. Am. Chem. Soc. 2007, 129, 13321;
27. g) B. M. Trost; R. C. Livingston, J. Am. Chem. Soc. 2008, 130, 11970,
28. M. R. Machacek, B. Faulk, J. Am. Chem. Soc. 2006, 128, 6745;
29. h) Y. Yamamoto, J. I. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2004, 126, 3712.
30. a) F. Monnier, C. Vovard-Le Bray, D. Castillo, V. Aubert, S. Dérien, P. H. Dixneuf, I. Toupet, A. Ienco, C. Mealli, J. Am. Chem. Soc. 2007, 129, 6037;
31. b) C. V. Bray, S. Dérien, P. H. Dixneuf, M. Murakami, Synlett 2008, 193;
32. c) J. Le Paih, S. Dérien, B. Demerseman, C. Bruneau, P. H. Dixneuf, L. Toupet, G. Dazinger, K. Kirchner, Chem. Eur. J. 2005, 11, 1312;
33. d) C. Vovard-Le Bray, S. Dérien, P. H. Dixneuf, Angew. Chem. 2009, DOI: 10.1002/ange.200805031;
34. Angew. Chem. Int. Ed. 2009, DOI: 10.1002/anie.200805031.
35. a) L. J. Gooßen, K. S. M. Salih, M. Blanchot, Angew. Chem. 2008, 120, 1;
36. Angew. Chem. Int. Ed. 2008, 47, 1;
37. b) K. Miki, M. Fujita, S. Uemura, K. Ohe, Org. Lett. 2006, 8, 1741;
38. c) K. Ohe, M. Fujita, H. Matsumoto, Y. Tai, K. Miki, J. Am. Chem. Soc. 2006, 128, 9270;
39. d) K. Fukamizu, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2008, 130, 10498;
40. e) B. M. Trost; R. C. Livingston, J. Am. Chem. Soc. 2008, 130, 11970.
41. For reviews on the Sonogashira reaction, see: a) R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874;
42. b) H. Doucet, J. C. Hierso, Angew. Chem. 2007, 119, 850;
43. Angew. Chem. Int. Ed. 2007, 46, 834;
44. c) R. R. Tykwinski, Angew. Chem. 2003, 115, 1604;
45. Angew. Chem. Int. Ed. 2003, 42, 1566.
46. J. Le Paih, F. Monnier, S. Derien, P. H. Dixneuf, E. Clot, O. Eisenstein, J. Am. Chem. Soc. 2003, 125, 11964.
47. a) K. Kirchner, M. J. Calhorda, R. Schmid, L. F. Veiros, J. Am. Chem. Soc. 2003, 125, 11721;
48. b) Y. Yamamoto, H. Kitahara, R. Ogawa, H. Kawaguchi, K. Tatsumi, K. Itoh, J. Am. Chem. Soc. 2000, 122, 4310;
49. c) J. A. Varela, L. Castedo, C. Saa, Org. Lett. 2003, 5, 2841;
50. d) Y. Yamamoto, K. Hata, T. Arakawa, K. Itoh, Chem. Commun. 2003, 1290;
51. e) Y. Yamamoto, H. Takagishi, K. Itoh, J. Am. Chem. Soc. 2002, 124, 28;
52. Y. Yamamoto, H. Takagishi, K. Itoh, J. Am. Chem. Soc. 2002, 124, 6844;
53. f) B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2002, 124, 4178;
54. g) B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2003, 125, 11516;
55. h) B. M. Trost, M. T. Rudd, M. G. Costa, P. I. Lee, A. E. Pomerantz, Org. Lett. 2004, 6, 4235.
56. For examples see: a) S. Danishefsky, Acc. Chem. Res. 1981, 14, 400;
57. b) B. Simoneau, P. Brassard, Tetrahedron 1986, 42, 3767;
58. c) T. Okabayashi, A. Iida, K. Takai, Y. Nawate, T. Misaki, Y. Tanabe, J. Org. Chem. 2007, 72, 8142;
59. d) H. Amii, T. Kobayashi, H. Terasawa, K. Uneyama, Org. Lett. 2001, 3, 3103;
60. e) A. K. Buzas, F. M. Istrate, F. Gagosz, Org. Lett. 2007, 9, 985;
61. f) S. Wang, L. Zhang, Org. Lett. 2006, 8, 4585;
62. g) G. Li, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 3740.
63. a) P. I. Dalko, L. Moisan, J. Cossy, Angew. Chem. 2002, 114, 647;
64. Angew. Chem. Int. Ed. 2002, 41, 625;
65. b) B. O. Ashburn, R. G. Carter, L. N. Zakharov, J. Am. Chem. Soc. 2007, 129, 9109;
66. c) K. Tiefenbacher, V. B. Arion, J. Mulzer, Angew. Chem. 2007, 119, 2744;
67. Angew. Chem. Int. Ed. 2007, 46, 2690;
68. d) J. C. Jewett, V. H. Rawal, Angew. Chem. 2007, 119, 6622;
69. Angew. Chem. Int. Ed. 2007, 46, 6502;
70. e) A. S. Batsanov, J. P. Knowles, A. P. Lightfoot, G. Maw, C. E. Thirsk, S. J. R. Twiddle, A. Whiting, Org. Lett. 2007, 9, 5565;
71. f) A. K. Ghosh, K. Xi, Org. Lett. 2007, 9, 4013;
72. g) D. Strübing, A. Kirschner, H. Neumann, S. Hübner, S. Klaus, D. Gördes, A. Jacobi von Wangelin, U. T. Bornscheuer, M. Beller, Chem. Eur. J. 2005, 11, 4210;
73. h) A. S. Dudnik, T. Schwier, V. Gevorgyan, Org. Lett. 2008, 10, 1465.
74. For selected recent examples of the synthesis of furans from alkynes see: a) S. A. K. Hashimi, M. Wolfle, F. Ata, M. Hamzic, R. Salathe, W. Frey, Adv. Synth. Catal. 2006, 348, 2501;
75. b) L. Ackermann, L. T. Kaspar, J. Org. Chem. 2007, 72, 6149;
76. c) E. Bustelo, P. H. Dixneuf, Adv. Synth. Catal. 2007, 349, 933;
77. d) J. Barluenga, L. Riesgo, R. Vicente, L. A. Lopez, M. Tomas, J. Am. Chem. Soc. 2008, 130, 13528.
78. The reaction with two different alkynes 1a and 1e led to the dissymmetric furan in 64% yield along with the symmetric ones 5a (20%) and 5e (16%).
79. Recent examples with copper(II) catalysis: a) S. Ueda, H. Nagasawa, Angew. Chem. 2008, 120, 6511;
80. Angew. Chem. Int. Ed. 2008, 47, 6411;
81. b) I. Ban, T. Sudo, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 3607;
82. c) W. C. P. Tsang, R. H. Munday, G. Brasche, N. Zheng, S. L. Buchwald, J. Org. Chem. 2008, 73, 7603;
83. d) B. Brasche, S. L. Buchwald, Angew. Chem. 2008, 120, 1958;
84. Angew. Chem. Int. Ed. 2008, 47, 1932;
85. e) W. J. Yoo, C. J. Li, J. Org. Chem. 2006, 71, 6266.