Amino Acid Promoted Ullmann Type Reaction with Low Catalyst Loading via Microwave Technology

K. Uma Maheshwar Reddy; K. Santosh Kumar; A. Panasa Reddy

doi:10.14233/ajchem.2014.16194

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Issue Published : July 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Amino Acid Promoted Ullmann Type Reaction with Low Catalyst Loading via Microwave Technology

https://doi.org/10.14233/ajchem.2014.16194

K. Uma Maheshwar Reddy

Department of Chemistry, University College of Engineering, Osmania University, Hyderabad-500 007, India

K. Santosh Kumar

Department of Chemistry, University College of Engineering, Osmania University, Hyderabad-500 007, India

A. Panasa Reddy

Department of Chemistry, University College of Engineering, Osmania University, Hyderabad-500 007, India

Corresponding Author(s) : A. Panasa Reddy

reddypanasa@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 15 (2014): Vol 26 Issue 15
Article Published : July 16, 2014

Abstract

This work describes CuBr-catalyzed cross-coupling of sterically hindered phenols with substituted aryl halides and hetero aryl halides under microwave conditions using commercially available amino acids as the reaction promoters and K₃PO₄ as the base. This protocol shown to tolerate sensitive functional groups like CN, CHO etc., Especially, in case of 3-bromopyridine coupling with substituted phenols supported this letter in track record of the reactivity.

Keywords

Aryl halide Phenol Ligand Microwave

Uma Maheshwar Reddy, K., Santosh Kumar, K., & Panasa Reddy, A. (2014). Amino Acid Promoted Ullmann Type Reaction with Low Catalyst Loading via Microwave Technology. Asian Journal of Chemistry, 26(15), 4747–4751. https://doi.org/10.14233/ajchem.2014.16194

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References

(a) J. Lindley, Tetrahedron, 40, 1433 (1984); doi:10.1016/S0040-4020(01)91791-0.; (b) A.V.R. Rao, M.K. Gurjar, K.L. Reddy and A.S. Rao, Chem. Rev., 95, 2135 (1995); doi:10.1021/cr00038a014.; (c) J. Scott Sawyer, Tetrahedron, 56, 5045 (2000); doi:10.1016/S0040-4020(00)00257-X.; (d) C. Zhong, J. He, C. Xue and Y. Li, Bioorg. Med. Chem., 12, 4009 (2004); doi:10.1016/j.bmc.2004.06.002.
(a) S.B. Singh and G.R. Pettit, J. Org. Chem., 55, 2797 (1990); doi:10.1021/jo00296a043.; (b) L. Liu, A. Siegmund, N. Xi, P. Kaplan-Lefko, K. Rex, A. Chen, J. Lin, J. Moriguchi, L. Berry, L. Huang, Y. Teffera, Y. Yang, Y. Zhang, S.F. Bellon, M. Lee, R. Shimanovich, A. Bak, C. Dominguez, M.H. Norman, J.-C. Harmange, I. Dussault and T.-S. Kim, J. Med. Chem., 51, 3688 (2008); doi:10.1021/jm800401t; (c) S. Caron, N.M. Do, J.E. Sieser, D.C. Whritenour and P.D. Hill, Org. Process Res. Dev., 13, 324 (2009); doi:10.1021/op800266x.; (d) F.F. Yong, Y.C. Teo, Y.K. Yan and G.L. Chua, Synlett, 101 (2012); doi:10.1055/s-0031-1290110; (e) W.M. Draper and J.E. Casida, J. Agric. Food Chem., 31, 1201 (1983); doi:10.1021/jf00120a015.; (f) C. Tomlin, The Pesticide Manual; Corp Protection Publication: Farnham, UK, edn 10 (1994).
(a) J. Lindley, Tetrahedron, 40, 1433 (1984); doi:10.1016/S0040-4020(01)91791-0; (b) F. Theil, Angew. Chem. Int. Ed., 38, 2345 (1999); doi:10.1002/(SICI)1521-3773(19990816)38:16<2345::AID-ANIE2345>3.0.CO;2-5.; (c) F. Thomas, S. Schulz, H. Mansikkamäki and M. Nieger, Angew. Chem. Int. Ed., 42, 5641 (2003); doi:10.1002/anie.200352332.
(a) F. Ullmann, Ber. Dtsch. Chem. Ges, 36, 2382 (1903); doi:10.1002/cber.190303602174.; (b) F. Ullmann, Chem. Ber., 37, 853 (1904); doi:10.1002/cber.190403701141.
H.J. Cristau, P. Cellier, S. Hamada, J.F. Spindler and M. Taillefer, Org. Lett., 6, 913 (2004); doi:10.1021/ol036290g.
(a) A. Kiyomori, J.F. Marcoux and S.L. Buchwald, Tetrahedron Lett., 40, 2657 (1999); doi:10.1016/S0040-4039(99)00291-9.; (b) T.D. Quach and R.A. Batey, Org. Lett., 5, 1381 (2003); doi:10.1021/ol034454n.
(a) R.K. Gujadhur, C.G. Bates and D. Venkataraman, Org. Lett., 3, 4315 (2001); doi:10.1021/ol0170105.; (b) E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante and P.J. Reider, Org. Lett., 4, 1623 (2002); doi:10.1021/ol025839t.
D. Ma and Q. Cai, Org. Lett., 5, 3799 (2003); doi:10.1021/ol0350947.
(a) P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan and A. Combs, Tetrahedron Lett., 39, 2941 (1998); doi:10.1016/S0040-4039(98)00504-8.; (b) D.A. Evans, J.L. Katz and T.R. West, Tetrahedron Lett., 39, 2937 (1998); doi:10.1016/S0040-4039(98)00502-4.
J.-F. Marcoux, S. Doye and S.L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); doi:10.1021/ja971901j.
(a) J.-F. Marcoux, S. Doye and S.L. Buchwald, J. Neurol. Neurosurg. Psychiatry, 55, 126 (1992); doi:10.1136/jnnp.55.2.126.; (b) W. Deng, Y. Xu and Q.X. Guo, Chin. Chem. Lett., 16, 327 (2005).
R.N. Gedye and J.B. Wei, Can. J. Chem., 76, 525 (1998); doi:10.1139/v98-075.
S. Noël, L. Djakovitch and C. Pinel, Tetrahedron Lett., 47, 3839 (2006); doi:10.1016/j.tetlet.2006.03.186

References

(a) J. Lindley, Tetrahedron, 40, 1433 (1984); doi:10.1016/S0040-4020(01)91791-0.; (b) A.V.R. Rao, M.K. Gurjar, K.L. Reddy and A.S. Rao, Chem. Rev., 95, 2135 (1995); doi:10.1021/cr00038a014.; (c) J. Scott Sawyer, Tetrahedron, 56, 5045 (2000); doi:10.1016/S0040-4020(00)00257-X.; (d) C. Zhong, J. He, C. Xue and Y. Li, Bioorg. Med. Chem., 12, 4009 (2004); doi:10.1016/j.bmc.2004.06.002.

(a) S.B. Singh and G.R. Pettit, J. Org. Chem., 55, 2797 (1990); doi:10.1021/jo00296a043.; (b) L. Liu, A. Siegmund, N. Xi, P. Kaplan-Lefko, K. Rex, A. Chen, J. Lin, J. Moriguchi, L. Berry, L. Huang, Y. Teffera, Y. Yang, Y. Zhang, S.F. Bellon, M. Lee, R. Shimanovich, A. Bak, C. Dominguez, M.H. Norman, J.-C. Harmange, I. Dussault and T.-S. Kim, J. Med. Chem., 51, 3688 (2008); doi:10.1021/jm800401t; (c) S. Caron, N.M. Do, J.E. Sieser, D.C. Whritenour and P.D. Hill, Org. Process Res. Dev., 13, 324 (2009); doi:10.1021/op800266x.; (d) F.F. Yong, Y.C. Teo, Y.K. Yan and G.L. Chua, Synlett, 101 (2012); doi:10.1055/s-0031-1290110; (e) W.M. Draper and J.E. Casida, J. Agric. Food Chem., 31, 1201 (1983); doi:10.1021/jf00120a015.; (f) C. Tomlin, The Pesticide Manual; Corp Protection Publication: Farnham, UK, edn 10 (1994).

(a) J. Lindley, Tetrahedron, 40, 1433 (1984); doi:10.1016/S0040-4020(01)91791-0; (b) F. Theil, Angew. Chem. Int. Ed., 38, 2345 (1999); doi:10.1002/(SICI)1521-3773(19990816)38:16<2345::AID-ANIE2345>3.0.CO;2-5.; (c) F. Thomas, S. Schulz, H. Mansikkamäki and M. Nieger, Angew. Chem. Int. Ed., 42, 5641 (2003); doi:10.1002/anie.200352332.

(a) F. Ullmann, Ber. Dtsch. Chem. Ges, 36, 2382 (1903); doi:10.1002/cber.190303602174.; (b) F. Ullmann, Chem. Ber., 37, 853 (1904); doi:10.1002/cber.190403701141.

H.J. Cristau, P. Cellier, S. Hamada, J.F. Spindler and M. Taillefer, Org. Lett., 6, 913 (2004); doi:10.1021/ol036290g.

(a) A. Kiyomori, J.F. Marcoux and S.L. Buchwald, Tetrahedron Lett., 40, 2657 (1999); doi:10.1016/S0040-4039(99)00291-9.; (b) T.D. Quach and R.A. Batey, Org. Lett., 5, 1381 (2003); doi:10.1021/ol034454n.

(a) R.K. Gujadhur, C.G. Bates and D. Venkataraman, Org. Lett., 3, 4315 (2001); doi:10.1021/ol0170105.; (b) E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante and P.J. Reider, Org. Lett., 4, 1623 (2002); doi:10.1021/ol025839t.

D. Ma and Q. Cai, Org. Lett., 5, 3799 (2003); doi:10.1021/ol0350947.

(a) P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan and A. Combs, Tetrahedron Lett., 39, 2941 (1998); doi:10.1016/S0040-4039(98)00504-8.; (b) D.A. Evans, J.L. Katz and T.R. West, Tetrahedron Lett., 39, 2937 (1998); doi:10.1016/S0040-4039(98)00502-4.

J.-F. Marcoux, S. Doye and S.L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997); doi:10.1021/ja971901j.

(a) J.-F. Marcoux, S. Doye and S.L. Buchwald, J. Neurol. Neurosurg. Psychiatry, 55, 126 (1992); doi:10.1136/jnnp.55.2.126.; (b) W. Deng, Y. Xu and Q.X. Guo, Chin. Chem. Lett., 16, 327 (2005).

R.N. Gedye and J.B. Wei, Can. J. Chem., 76, 525 (1998); doi:10.1139/v98-075.

S. Noël, L. Djakovitch and C. Pinel, Tetrahedron Lett., 47, 3839 (2006); doi:10.1016/j.tetlet.2006.03.186

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Amino Acid Promoted Ullmann Type Reaction with Low Catalyst Loading via Microwave Technology

Corresponding Author(s) : A. Panasa Reddy

Abstract

Keywords

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