Transition-metal-free homocoupling of 1-haloalkynes: A facile synthesis of symmetrical 1,3-diynes

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6700-6703

  Chen, Zhengwang ^a   Jiang, Huanfeng ^a   Wang, Azhong ^a   Yang, Shaorong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIYNE COMPOUNDS; FACILE SYNTHESIS; HIGH YIELD; HOMOCOUPLING; HOMOCOUPLING REACTIONS;

FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL);

TRANSITION METALS;

1 HALOALKYNE DERIVATIVE; 1,4 DIPHENYLBUTA 1,3 DIYNE; ALKYNE DERIVATIVE; FUNCTIONAL GROUP; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HOMOCOUPLING REACTION; SYNTHESIS;

ALKYNES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77957167367     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101216m     Document Type: Article

References (64)

1. Tour, J. M. Chem. Rev. 1996, 96, 537-553
2. Nielsen, M. B.; Diederich, F. Chem. Rev. 2005, 105, 1837-1867
3. Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377
4. For reviews, see: Shi Shun, A. L. K.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034-1057
5. Bohlmann, F.; Burkhardt, T.; Zdero, C. In Naturally Occurring Acetylenes; Academic Press: New York, 1973.
6. Carbon-Rich Compounds: From Molecules to Materials; Haley, M. M.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
7. Acetylene Chemistry: Chemistry, Biology and Material Science; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
8. Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
9. Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422-424
10. Glaser, C. Ann. Chem. Pharm. 1870, 154, 137-171
11. Eglinton, G.; Galbraith, A. R. Chem. Ind. 1956, 737-738
12. Hay, A. S. J. Org. Chem. 1960, 25, 1275-1276
13. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321
14. For recent representative papers on copper-catalyzed homocoupling from terminal alkynes, see: Jiang, H.-F.; Tang, J.-Y.; Wang, A. Z.; Deng, G.-H.; Yang, S.-R. Synthesis 2006, 1155-1161
15. Li, J.; Jiang, H. Chem. Commun. 1999, 2369-2370
16. Kamata, K.; Yamaguchi, S.; Kotani, M.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407-2410
17. Adimurthy, S.; Malakar, C. C.; Beifuss, U. J. Org. Chem. 2009, 74, 5648-5651
18. Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709-712
19. Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909-912
20. Li, D.; Yin, K.; Li, J.; Jia, X. Tetrahedron Lett. 2008, 49, 5918-5919
21. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Gayathri, K. U.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493-6496
22. Li, L.; Wang, J.; Zhang, G.; Liu, Q. Tetrahedron Lett. 2009, 50, 4033-4036
23. Yamaguchi, K.; Kamata, K.; Yamaguchi, S.; Miyuki Kotani, M.; Mizuno, N. J. Catal. 2008, 258, 121-130
24. For recent representative papers on copper-catalyzed homocoupling from internal alkynes, see: Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Atsunori Mori, A.; Hiyama, Y. J. Org. Chem. 2000, 65, 1780-1787
25. Paixão, M. W.; Weber, M.; Braga, A. L.; de Azeredo, J. B.; Deobald, A. M.; Stefani, H. A. Tetrahedron Lett. 2008, 49, 2366-2370
26. Nishihara, Y.; Okamoto, M.; Inoue, Y.; Miyazaki, M.; Miyasaka, M.; Takagi, K. Tetrahedron Lett. 2005, 46, 8661-8664
27. For recent representative papers on palladium-catalyzed homocoupling from terminal alkynes, see: Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523-526
28. Vlassa, M.; Ciocan-Tarta, I.; Margineanu, F.; Oprean, I. Tetrahedron 1996, 52, 1337-1342
29. Liu, Q.' Burton, D. J. Tetrahedron Lett. 1997, 38, 4371-4374
30. Lei, A.; Srivastava, M.; Zhang, X. J. Org. Chem. 2002, 67, 1969-1971
31. Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632-633
32. Batsanov, A. S.; Collings, J. C.; Fairlamb, I. J. S.; Holland, J. P.; Howard, J. A. K.; Lin, Z.; Marder, T. B.; Parsons, A. C.; Ward, R. M.; Zhu, J. J. Org. Chem. 2005, 70, 703-706
33. Chen, S.-N.; Wu, W.-Y.; Tsai, F.-Y. Green Chem. 2009, 11, 269-274
34. Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2005, 70, 4393-4396
35. Li, J.-H.; Liang, Y.; Zhang, X.-D. Tetrahedron 2005, 61, 1903-1907
36. Yan, J.; Wu, J.; Jin, H. J. Organomet. Chem. 2007, 692, 3636-3639
37. Yang, F.; Cui, X.; Li, Y.; Zhang, J.; Ren, G.; Wu, Y. Tetrahedron 2007, 63, 1963-1969
38. Shi, M.; Qian, H. Appl. Organomet. Chem. 2006, 20, 771-774
39. For recent representative papers on palladium-catalyzed homocoupling from internal alkynes, see: Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510-1511
40. Damle, S. V.; Seomoon, D.; Lee, P. H. J. Org. Chem. 2003, 68, 7085-7087
41. Singh, F. V.; Amaral, M. F. Z. J.; Stefani, H. A. Tetrahedron Lett. 2009, 50, 2636-2639
42. Oh, C. H.; Reddy, V. R. Tetrahedron Lett. 2004, 45, 5221-5224
43. Shirakawa, E.; Nakao, Y.; Murota, Y.; Hiyama, T. J. Organomet. Chem. 2003, 670, 132-136
44. Cahiez, G.; Moyeux, A.; Buendia, J.; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788-13789
45. Bharathi, P.; Periasamy, M. Organometallics 2000, 19, 5511-5513
46. Ishikawa, T.; Ogawa, A.; Hirao, T. Organometallics 1998, 17, 5713-5716
47. Krasovskiy, A.; Tishkov, A.; del Amo, V.; Mayr, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 501'-5014
48. Maji, M. S.; Pfeifer, T.; Studer, A. Angew. Chem., Int. Ed. 2008, 47, 9547-9550
49. For selective examples, see: Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742-7743
50. Trofimov, A.; Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 13538-13539
51. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250-3252
52. Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156-4159
53. Morishita, T.; Yoshida, H.; Ohshita, J. Chem. Commun. 2010, 640-642
54. Li, Y.; Liu, X.; Jiang, H.; Feng, Z. Angew. Chem., Int. Ed. 2010, 49, 3338-3341
55. Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 597 - 647.
56. Jiang, H.; Wang, A. Synthesis 2007, 1649-1654
57. For selective examples, see: Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017
58. Shi, W.; Luo, Y.; Luo, X.; Chao, L.; Zhang, H.; Wang, J.; Lei, A. J. Am. Chem. Soc. 2008, 130, 14713-14720
59. Marino, J. P.; Nguyen, H. N. J. Org. Chem. 2002, 67, 6841-6844
60. Luu, T.; Morisaki, Y.; Cunningham, N.; Tykwinski, R. R. J. Org. Chem. 2007, 72, 9622-9629
61. Negishi, E.; Hata, M.; Xu, C. Org. Lett. 2000, 2, 3687-3689
62. Kim, S.; Kim, S.; Lee, T.; Ko, H.; Kim, D. Org. Lett. 2004, 6, 3601-3604
63. Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709-712
64. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657