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This work is licensed under a Creative Commons Attribution 4.0 International License.
3-(Diphenylphosphino)propanoic Acid: An Efficient Ligand for Cu-Catalyzed N-Arylations of Indoles and Aryl Amines
Corresponding Author(s) : P. Liu
Asian Journal of Chemistry,
Vol. 27 No. 3 (2015): Vol 27 Issue 3
Abstract
3-(Diphenylphosphino)propanoic acid (L2) was found to be an efficient ligand for the copper-catalyzed N-arylations of indoles and arylamines with aryl iodides, the C-N coupling reactions catalyzed by CuCl/L2 were smoothly carried out in DMSO at 120 ºC and give the corresponding products with the yields of 25-98 %.
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- M. Yang and F. Liu, J. Org. Chem., 72, 8969 (2007); doi:10.1021/jo0712291.
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- A. Bader and E. Lindner, Coord. Chem. Rev., 108, 27 (1991); doi:10.1016/0010-8545(91)80013-4.
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- K. Issleib and G. Thomas, Z. Anorg. Allg. Chem., 330, 295 (1964); doi:10.1002/zaac.19643300509.
- K. Issleib and G. Thomas, Chem. Ber., 93, 803 (1960); doi:10.1002/cber.19600930409.
References
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J.F. Hartwig, in ed: A. Ricci, Modern Amination Methods, Wiley-VCH, Weinheim, p. 195 (2000).
J.P. Wolfe and S.L. Buchwald, J. Am. Chem. Soc., 119, 6054 (1997); doi:10.1021/ja964391m.
C. Desmarets, R. Schneider and Y. Fort, J. Org. Chem., 67, 3029 (2002); doi:10.1021/jo016352l.
S. Tasler and B.H. Lipshutz, J. Org. Chem., 68, 1190 (2003); doi:10.1021/jo020297e.
F. Monnier and M. Taillefer, Angew. Chem. Int. Ed., 48, 6954 (2009); doi:10.1002/anie.200804497.
M.G. Boswell, F.G. Yeung and C. Wolf, Synlett, 1240 (2012); doi:10.1055/s-0031-1290827.
Y.-C. Teo, F.-F. Yong and G.S. Lim, Tetrahedron Lett., 52, 7171 (2011); doi:10.1016/j.tetlet.2011.10.128.
R.K. Gujadhur, D. Venkataraman and J.T. Kintigh, Tetrahedron Lett., 42, 4791 (2001); doi:10.1016/S0040-4039(01)00888-7.
R.K. Gujadhur, C.G. Bates and D. Venkataraman, Org. Lett., 3, 4315 (2001); doi:10.1021/ol0170105.
M. Yang and F. Liu, J. Org. Chem., 72, 8969 (2007); doi:10.1021/jo0712291.
A. Kiyomori, J.-F. Marcoux and S.L. Buchwald, Tetrahedron Lett., 40, 2657 (1999); doi:10.1016/S0040-4039(99)00291-9.
L. Liu, M. Frohn, N. Xi, C. Dominguez, R. Hungate and P.J. Reider, J. Org. Chem., 70, 10135 (2005); doi:10.1021/jo051640t.
A.A. Kelkar, N.M. Patil and R.V. Chaudhari, Tetrahedron Lett., 43, 7143 (2002); doi:10.1016/S0040-4039(02)01708-2.
Y.-H. Liu, C. Chen and L.-M. Yang, Tetrahedron Lett., 47, 9275 (2006); doi:10.1016/j.tetlet.2006.10.103.
J.C. Antilla, A. Klapars and S.L. Buchwald, J. Am. Chem. Soc., 124, 11684 (2002); doi:10.1021/ja027433h.
A. Klapars, X. Huang and S.L. Buchwald, J. Am. Chem. Soc., 124, 7421 (2002); doi:10.1021/ja0260465.
B. Mallesham, B.M. Rajesh, P.R. Reddy, D. Srinivas and S. Trehan, Org. Lett., 5, 963 (2003); doi:10.1021/ol026902h.
P.-S. Wang, C.-K. Liang and M.-K. Leung, Tetrahedron, 61, 2931 (2005); doi:10.1016/j.tet.2005.01.063.
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P.E. Maligres, S.W. Krska and P.G. Dormer, J. Org. Chem., 77, 7646 (2012); doi:10.1021/jo300905w.
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Y.-J. Chen and H.-H. Chen, Org. Lett., 8, 5609 (2006); doi:10.1021/ol062339h.
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H.-J. Cristau, P.P. Cellier, J.-F. Spindler and M. Taillefer, Chem. Eur. J., 10, 5607 (2004); doi:10.1002/chem.200400582.
Z.Q. Wu, Z.Q. Jiang, D. Wu, H.F. Xiang and X.G. Zhou, Eur. J. Org. Chem., 2010, 1854 (2010); doi:10.1002/ejoc.201000060.
Z.Q. Wu, L. Zhou, Z.Q. Jiang, D. Wu, Z.K. Li and X.G. Zhou, Eur. J. Org. Chem., 2010, 4971 (2010); doi:10.1002/ejoc.201000840.
Y. Wang, Z. Wu, L.X. Wang, Z.K. Li and X.G. Zhou, Chem. Eur. J., 15, 8971 (2009); doi:10.1002/chem.200901232.
D. Ma, Q. Cai and H. Zhang, Org. Lett., 5, 2453 (2003); doi:10.1021/ol0346584.
D. Ma and Q. Cai, Synlett, 128 (2004); doi:10.1055/s-2003-44995.
Q. Cai, W. Zhu, H. Zhang, Y. Zhang and D. Ma, Synthesis, 496 (2005); doi:10.1055/s-2004-831196.
H. Zhang, Q. Cai and D. Ma, J. Org. Chem., 70, 5164 (2005); doi:10.1021/jo0504464.
X. Lv, Z. Wang and W. Bao, Tetrahedron, 62, 4756 (2006); doi:10.1016/j.tet.2006.03.026.
Z. Lu, R.J. Twieg and S.D. Huang, Tetrahedron Lett., 44, 6289 (2003); doi:10.1016/S0040-4039(03)01536-3.
Z. Lu and R. Twieg, Tetrahedron Lett., 46, 2997 (2005); doi:10.1016/j.tetlet.2005.03.027.
H. Rao, H. Fu, Y. Jiang and Y. Zhao, J. Org. Chem., 70, 8107 (2005); doi:10.1021/jo051221w.
W. Keim, Chem. Ing. Techn., 56, 850 (1984); doi:10.1002/cite.330561108.
X. Du, X.J. Feng, Y. Liu, R. He and M. Bao, Chin. Chem. Lett., 21, 641 (2010); doi:10.1016/j.cclet.2010.01.042.
L. Zhou, Q. Miao, R. He, X.J. Feng and M. Bao, Tetrahedron Lett., 48, 7899 (2007); doi:10.1016/j.tetlet.2007.08.089.
M.P. Guo, F.F. Jian and R. He, J. Fluor. Chem., 127, 177 (2006); doi:10.1016/j.jfluchem.2005.09.003.
M.P. Guo, F.F. Jian and R. He, Tetrahedron Lett., 46, 9017 (2005); doi:10.1016/j.tetlet.2005.10.104.
E. Ullah, J. McNulty and A. Robertson, Tetrahedron Lett., 50, 5599 (2009); doi:10.1016/j.tetlet.2009.07.088.
A. Bader and E. Lindner, Coord. Chem. Rev., 108, 27 (1991); doi:10.1016/0010-8545(91)80013-4.
G.J.P. Britovsek, W. Keim, S. Mecking, D. Sainz and T. Wagner, J. Chem. Soc. Chem. Commun., 1632 (1993); doi:10.1039/c39930001632.
Y. Liu, W. Liu, Q. Zhang, P. Liu, J.-W. Xie and B. Dai, J. Chem. Res., 37, 636 (2013); doi:10.3184/174751913X13795203316679.
Y. Liu, Q. Zhang, X.-W. Ma, P. Liu, J.-W. Xie, B. Dai and Z.-Y. Liu, Int. J. Org. Chem., 3, 185 (2013); doi:10.4236/ijoc.2013.33023.
Y.-S. Liu, Y. Liu, X.-W. Ma, P. Liu, J.-W. Xie and B. Dai, Chin. Chem. Lett., 25, 775 (2014); doi:10.1016/j.cclet.2014.01.042.
K. Issleib and G. Thomas, Z. Anorg. Allg. Chem., 330, 295 (1964); doi:10.1002/zaac.19643300509.
K. Issleib and G. Thomas, Chem. Ber., 93, 803 (1960); doi:10.1002/cber.19600930409.