Utility of dysprosium as a reductant in coupling reactions of acyl chlorides: The synthesis of amides and diaryl-substituted acetylenes

Organometallics

Volumn 30, Issue 7, 2011, Pages 2026-2030

  Chen, Weifeng ^a   Li, Kebin ^a   Hu, Ziqiang ^a   Wang, Liliang ^a   Lai, Guoqiao ^a   Li, Zhifang ^a  

^a HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL CHLORIDES; COUPLING REACTION; CROSS-COUPLINGS; GOOD YIELD; N ,N-DIMETHYLACETAMIDE; PRE-TREATMENT; REDUCTANTS; SUBSTITUTED ACETYLENES; SYNTHESIS OF AMIDE;

ACETYLENE; AMIDES; DYSPROSIUM; LIGHTING; SYNTHESIS (CHEMICAL);

CHLORINE COMPOUNDS;

EID: 79953690862     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200080f     Document Type: Article

References (69)

1. Namy, J. L.; Girard, P.; Kagan, H. B. New J. Chem. 1977, 1, 5-7
2. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698
3. Namy, J. L.; Girard, P.; Kagan, H. B.; Caro, P. E. New J. Chem. 1981, 5, 479-484
4. Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, K. A., Jr.; Eyring, L., Eds.; Elsevier: Amsterdam, 1984; Vol. 6, Chapter 50.
5. For reviews, see: Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614
6. Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23
7. Molander, G. A. Chem. Rev. 1992, 92, 29-68
8. Krief, A.; Laval, A. M. Chem. Rev. 1999, 99, 745-777
9. Molander, G. A.; Harris, C. R. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 6, pp 4428 - 4432.
10. Jung, D. Y; Kim, Y. H. Synlett 2005, 3019-3032
11. Gopalaiah, K.; Kagan, H. B. New J. Chem. 2008, 32, 607-637
12. Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140-7165
13. Concellon, J. M.; Rodriguez-Solla, H.; Concellon, C.; del Amo, V. Chem. Soc. Rev. 2010, 53, 1914-1920
14. Gong, H. J.; Jia, X. S.; Zai, H. B. Chin. J. Org. Chem. 2010, 30, 939-950
15. Otsubo, K.; Inanaga, J.; Yamaguchi, N. Tetrahedron Lett. 1986, 57, 4437
16. Flowers, R. A.; Shabangi, M. Tetrahedron Lett. 1997, 38, 1137
17. Vogel, E. W.; Van Zeeland, A. A.; Raaymakers Jansen Verplanke, C. A.; Zijlstra, J. A. Mutat. Res. 1985, 150, 241-260
18. Evans, W. J.; Workman, P. S.; Allen, N. T. Org. Lett. 2003, 5, 2041-2042
19. Burin, M. E.; Smirnova, M. V.; Fukin, G. K.; Baranov, E. V.; Bochkarev, M. N. Eur. J. Inorg. Chem. 2006, 351-356
20. Fagin, A. A.; Balashova, T. V.; Kusyaev, D. M.; Kulikova, T. I.; Glukhova, T. A.; Makarenko, N. P.; Kurskii, Y. A.; Evans, W. J.; Bochkarev, M. N. Polyhedron 2006, 25, 1105-1110
21. Jaroschik, F.; Momin, A.; Nief, F.; Le Goff, X. F.; Deacon, G. B.; Junk, P. C. Angew. Chem., Int. Ed. 2009, 48, 1117-1121
22. Bochkarev, M. N.; Fagin, A. A. Chem.Eur. J. 1999, 5, 2990-2992
23. Evans, W. J.; Allen, N. T.; Ziller, J. W. J. Am. Chem. Soc. 2000, 122, 11749-11750
24. Xiang, X.; Shen, Q. S.; Wang, J. L.; Zhu, Z. Y.; Huang, W.; Zhou, X. G. Organometallics 2008, 27, 1959-1962
25. Bochkarev, M. N.; Fedushkin, I. L.; Fagin, A. A.; Petrovskaya, T. V.; Ziller, J. W.; Broomhall-Dillard, R. N.; Evans, W. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 133-135
26. Evans, W. J.; Allen, N. T. J. Am. Chem. Soc. 2000, 122, 2118-2119
27. Turcitu, D.; Nief, F.; Ricard, L. Chem.Eur. J. 2003, 9, 4916-4923
28. Morss, L. R. Chem. Rev. 1976, 76, 827
29. Evans, W. J.; Allen, N. T.; Ziller, J. W. J. Am. Chem. Soc. 2001, 123, 7927-7928
30. Bochkarev, M. N.; Fedushin, I. L.; Dechert, S.; Fagin, A. A.; Schumann, H. Angew. Chem., Int. Ed. 2001, 40, 3176
31. Izod, K. Angew. Chem., Int. Ed. 2002, 41, 743
32. Evans, W. J.; Allen, N. T.; Ziller, J. W. Angew. Chem., Int. Ed. 2002, 41, 359
33. Evans, W. J.; Zucchi, G.; Ziller, J. W. J. Am. Chem. Soc. 2003, 125, 10-11
34. Bochkarev, M. N.; khoroshenkov, G. V.; Schumann, H.; Dechert, S. J. Am. Chem. Soc. 2003, 125, 2894-2895
35. Katkova, M. A.; Fukin, G. K.; Fagin, A. A.; Bochkarev, M. N. J. Organomet. Chem. 2003, 682, 218-223
36. Bochkarev, M. N. Coord. Chem. Rev. 2004, 248, 835
37. Jaroschik, F.; Momin, A.; Nief, F.; Le Goff, X. F.; Deacon, G. B.; Junk, P. C. Angew. Chem., Int. Ed. 2009, 48, 1117-1121
38. Nief, F. Dalton Trans. 2010, 39, 6589-6598
39. Imamoto, T.; Kusumoto, T.; Hatanaka, Y.; Yokoyama, M. Tetrahedron Lett. 1982, 23, 1353
40. Yanada, R.; Negoro, N.; Okaniwa, M.; Ibuka, T. Tetrahedron 1999, 55, 13947
41. Nishino, T.; Nishiyama, Y.; Sonada, N. J. Org. Chem. 2002, 67, 966
42. Nishino, T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.; Sonada, N. J. Org. Chem. 2002, 67, 8696
43. Taniguchi, Y.; Kuno, T.; Nakahashi, M.; Takaki, K.; Fujiwara, Y. Appl. Organomet. Chem. 1995, 9, 491
44. Jin, W. S.; Makioka, Y.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2001, 66, 514
45. Wang, L.; Zhang, Y. Tetrahedron 1998, 54, 11129-11140
46. Zhu, Z. Y.; Wang, J. L.; Zhang, Z. X.; Xiang, X.; Zhou, X. G. Organometallics 2002, 26, 2499-2500
47. Talukdar, S.; Fang, J. M. J. Org. Chem. 2001, 66, 330
48. Ghatak, A.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 3793-3796
49. Ogawa, A.; Sumino, Y.; Nanke, T.; Ohya, S.; Sonada, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 2745
50. Ogawa, A.; Ohya, S.; Hirao, T. Chem. Lett. 1997, 275
51. Sumino, Y.; Harato, N.; Tomisaka, Y.; Ogawa, A. Tetrahedron 2003, 59, 10499
52. Tomisaka, Y.; Nomoto, A.; Ogawa, A. Tetrahedron Lett. 2009, 50, 584-586
53. Li, Z.; Tomisaka, Y.; Nomoto, A.; Zhang, Y.; Ogawa, A. Chem. Lett. 2009, 16-17
54. Flood, T. C. Tetrahedron Lett. 1977, 18, 3861-3864
55. Dams, R.; Malinowski, M.; Westdorp, I.; Geise, H. J. J. Org. Chem. 1981, 46, 2406-2407
56. Girard, P.; Couffignal, R.; Kagan, H. B. Tetrahedron Lett. 1981, 22, 3959-3960
57. Souppe, J.; Namy, J. L.; Kagan, H. B. Tetrahedron Lett. 1984, 25, 2869-2872
58. Collin, J.; Namy, J. L.; Dallemer, F.; Kagan, H. B. J. Org. Chem. 1991, 56, 3118-3122
59. Namy, J. L.; Colomb, M.; Kagan, H. B. Tetrahedron Lett. 1994, 35, 1723-1726
60. Li, Z.; Zhang, Y. Chin. J. Chem. 2001, 19, 634-636
61. Liu, Y.; Wang, X.; Zhang, Y. Synth. Commun. 2004, 34, 4009-4022
62. Horner, L.; Dickerhof, K. Chem. Ber. 1983, 116, 1615-1622
63. Polo, C.; Quintanilla, G. M.; Barba, F. Synth. Commun. 1994, 24, 907-915
64. Hydrazine-induced deoxygenation of α-diketones: Cope, A. C.; Smith, D. S.; Cotter, R. J. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 377.
65. Barton, H. R. D.; Bashiardes, G.; Fourrey, J. L. Tetrahdron 1988, 44, 147-162
66. Xue, Z.; Sieber, W. J.; Knobler, C. B.; Daesz, H. D. J. Am. Chem. Soc. 1990, 112, 1825-1833
67. Active uranium-induced reduction of dicarbonyls: Kahn, B. E.; Reike, R. D. J. Organomet. Chem. 1988, 346, C45-48
68. Busacca, C. A.; Farber, E.; Deyoung, J.; Campbell, S.; Gonnella, N. C.; Grinberg, N.; Haddad, N.; Lee, H.; Ma, S.; Reeves, D.; Shen, S.; Senanayake, C. H. Org. Lett. 2009, 11, 5594-5597
69. Volodymyr, S.; Jolanta, L.; Karol, G.. J. Org. Chem. 2004, 69, 7748-7751