Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents

Chemical Communications

Volumn 49, Issue 94, 2013, Pages 11101-11103

  Kim, Ju Hyun ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ALKYNE; BROMIDE; CHLORIDE; COPPER; COPPER OXIDE; GRIGNARD REAGENT; HALIDE; NANOPARTICLE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; PARTICLE SIZE; SYNTHESIS;

EID: 84887042662     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc46419a     Document Type: Article

References (45)

1. A. Suzuki, Pure Appl. Chem. 1985 57 1749
2. R. F. Heck, Org. React. 1982 27 345
3. D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1979 101 4981
4. E. I. Negishi and F. Liu, in Metal-Catalyzed Cross-Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, Germany, 1998, pp. 1-47
5. E. Negishi, Acc. Chem. Res. 1982 15 340
6. E. Erdik, Tetrahedron 1992 48 9577
7. Y. Nakao, T. Hiyama, Chem. Soc. Rev. 2011 40 4893
8. A. Devasagayaraj, T. Studemann, P. Knochel, Angew. Chem. Int. Ed. Engl. 1995 34 2723
9. K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972 94 4374
10. K. Tamao, Y. Kiso, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972 94 9268-9269
11. R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144
12. J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 890
13. H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 2008 10 969
14. H. Someya, H. Yorimitsu, K. Oshima, Tetrahedron Lett. 2009 50 3270
15. K. G. Dongol, H. Koh, M. Sau, C. L. L. Chai, Adv. Synth. Catal. 2007 349 1015
16. M. G. Cenios, F. Tato, E. Bunuel, P. Calle, D. J. Cárdenas, Chem. Sci. 2013 4 1098
17. P. Ren, O. Vechokin, K. von Allmen, R. Scopelliti, X. Hu, J. Am. Chem. Soc. 2011 133 7084
18. T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 2002 41 4137
19. S. P. Singh, J. Terao, N. Kambe, Tetrahedron Lett. 2009 50 5644
20. R. Shimizu, E. Yoneda, T. Fuchikami, Tetrahedron Lett. 1996 37 5557
21. G. Cahiez, O. Gager, J. Buendia, Synlett 2010, 299
22. M.-B. Li, X.-L. Tang, S.-K. Tian, Adv. Synth. Catal. 2011 353 1980
23. M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972 42 205
24. G. Cahiez, C. Chaboche, M. JÉzÉquel, Tetrahedron 2000 56 2733
25. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002 124 4222
26. J. Terao, A. Oda, A. Ikumi, A. Nakamura, H. Kuniyasu, N. Kambe, Angew. Chem. Int. Ed. 2003 42 3412
27. J. Terao, H. Todo, H. Watanabe, A. Ikumi, N. Kambe, Angew. Chem. Int. Ed. 2004 43 6180
28. J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003 125 5646
29. J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe, Angew. Chem. Int. Ed. 2007 46 2086
30. G. Cahiez, C. Chaboche, A. Gilliani, C. Duplais, A. Moyeux, Adv. Synth. Catal. 2008 350 1484
31. P. Ren, L.-A. Stem, X. Hu, Angew. Chem. Int. Ed. 2012 51 9110
32. C.-T. Yang, Z.-Q. Zhang, J. Liang, J.-H. Liu, X.-Y. Lu, H.-H. Chen, L. Liu, J. Am. Chem. Soc. 2012 134 11124
33. T. Iwasaki, H. Takagawa, S. P. Singh, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2013 135 9604
34. J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2013 135 10602
35. J. H. Park, Y. K. Chung, Dalton Trans. 2008, 2369
36. O. Vechorkin, V. Proust, X. Hu, J. Am. Chem. Soc. 2009 131 9756
37. D. H. Burns, J. D. Miller, H. K. Chan, M. O. Delaney, J. Am. Chem. Soc. 1997 119 2125
38. G. Cahiez, O. Gager, J. Buendia, Synlett 2010, 299
39. I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004 248 2337
40. J. Terao, N. Kambe, Acc. Chem. Res. 2008 41 1545
41. M. A. Blitz, S. A. Mitchell, P. A. Hackett, J. Phys. Chem. 1993 97 5298
42. J. A. Howard, R. Sutcliffe, J. S. Tse, B. Mile, Organometallics 1984 3 859
43. J. O. Metzger, R. Mahler, Angew. Chem. Int. Ed. Engl. 1995 34 902.
44. B. C. Ranu, A. Saha, R. Jana, Adv. Synth. Catal. 2007 349 2690
45. G. Cahiez, O. Gager, J. Buendia, Angew. Chem. Int. Ed. 2010 49 1278