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Iron-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Biphenyl Grignard Reagent
Corresponding Author(s) : Z.Y. Zhang
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
In the presence of a catalytic amount of iron salts and N,N,N',N'-tetramethylethylene diamine as additive, alkyl bromide reacted with biphenyl magnesium bromide to obtain the cross-coupling product in good yields. The suitable amount of catalyst and the additive are 5 % mol (based on alkyl bromide), 1.3 equiv(based on alkyl bromide), respectively. Under the optimal conditions, the yields of the cross-coupling could reach up to 92.3 %.
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- V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner and P. Knochel, Tetrahedron Lett., 42, 5717 (2001).
- A.C. Frisch and M. Beller, Angew. Chem., 117, 680 (2005).
- G. Cahiez, C. Chaboche and M. Jezequel, Tetrahedron, 56, 2733 (2000).
- D. Hauk, S. Lang and A. Murso, Org. Process Res. Devlop., 10, 733 (2006).
- J. Terao, A. Ikumi, H. Kuniyasu and N. Kambe, J. Am. Chem. Soc., 125, 5646 (2003).
- J. Terao, H. Todo, S.A. Begum, H. Kuniyasu and N. Kambe, Angew. Chem. Int. Ed., 46, 2086 (2007).
- J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu and N. Kambe, J. Am. Chem. Soc., 124, 4222 (2002).
- C. Gottardo and A. Aguirre, Tetrahedron Lett., 43, 7091 (2002).
- J. Quintin, X. Franck, R. Hocquemiller and B. Figadère, Tetrahedron Lett., 43, 3547 (2002).
- J.W. Dankwardt, J. Organomet. Chem., 690, 932 (2005).
- G. Wang, Z.Y. Zhang, K.C. Zhang, B.-M. Wei and Z.Q. Dai, Chin. J. Org. Chem., 28, 538 (2008).
- Z.Q. Dai, W.W. Zhang, Z.Y. Zhang and Y.K. Yang, Asian J. Chem., 23, 4087 (2011)
References
V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner and P. Knochel, Tetrahedron Lett., 42, 5717 (2001).
A.C. Frisch and M. Beller, Angew. Chem., 117, 680 (2005).
G. Cahiez, C. Chaboche and M. Jezequel, Tetrahedron, 56, 2733 (2000).
D. Hauk, S. Lang and A. Murso, Org. Process Res. Devlop., 10, 733 (2006).
J. Terao, A. Ikumi, H. Kuniyasu and N. Kambe, J. Am. Chem. Soc., 125, 5646 (2003).
J. Terao, H. Todo, S.A. Begum, H. Kuniyasu and N. Kambe, Angew. Chem. Int. Ed., 46, 2086 (2007).
J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu and N. Kambe, J. Am. Chem. Soc., 124, 4222 (2002).
C. Gottardo and A. Aguirre, Tetrahedron Lett., 43, 7091 (2002).
J. Quintin, X. Franck, R. Hocquemiller and B. Figadère, Tetrahedron Lett., 43, 3547 (2002).
J.W. Dankwardt, J. Organomet. Chem., 690, 932 (2005).
G. Wang, Z.Y. Zhang, K.C. Zhang, B.-M. Wei and Z.Q. Dai, Chin. J. Org. Chem., 28, 538 (2008).
Z.Q. Dai, W.W. Zhang, Z.Y. Zhang and Y.K. Yang, Asian J. Chem., 23, 4087 (2011)