Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

Copyright (c) 2014 AJC

Creative Commons License

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

Pd/C-Catalyzed Ligand-Free Hiyama Cross-Coupling Reaction of Aryl Halides Under Aqueous Conditions

https://doi.org/10.14233/ajchem.2014.15797
Nagaraju Mittapelly
Inogent Laboratories Private Limited, A GVK BIO Company, 28A, IDA, Nacharam, Hyderabad-500 076, India ;Centre for Chemical Sciences and Technology, I.S.T. Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India
Khagga Mukkanti
Centre for Chemical Sciences and Technology, I.S.T. Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India
Buchi Reddy Reguri
Orchid Chemicals and Pharmaceuticals Ltd., Sholinganallur, Chennai-600 119, India

Corresponding Author(s) : Nagaraju Mittapelly

nagunitrogen@yahoo.co.in

Asian Journal of Chemistry, Vol. 26 No. 4 (2014): Vol 26 Issue 4

Abstract

A mild and efficient ligand-free Hiyama cross-coupling reaction using Pd/C as a catalyst under aqueous conditions has been developed. A wide variety of aryl bromides undergo the cross-coupling with aryl siloxanes in excellent yields without the use of any additives. The operational simplicity and the mild reaction conditions add to the value of this method as a practical alternative to the Hiyama cross-coupling of aryl and heteroaryl halides.

Keywords

Hiyama cross-coupling Aryl halide Pd/C
Mittapelly, N., Mukkanti, K., & Reddy Reguri, B. (2014). Pd/C-Catalyzed Ligand-Free Hiyama Cross-Coupling Reaction of Aryl Halides Under Aqueous Conditions. Asian Journal of Chemistry, 26(4), 1015–1018. https://doi.org/10.14233/ajchem.2014.15797
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. (a) D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); doi:10.1021/cr020033s.; (b) G. Bringmann, C. Gunther, M. Ochse, O. Schupp and S. Tasler, in eds: W. Herz, H. Falk, G.W. Kirby and R.E. Moore, Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites In: Progress in the Chemistry of Organic Natural Products, Springer-Verlag: New York, Volume 82 (2001); (c) P.J. Hajduk, M. Bures, J. Praestgaard and S.W. Fesik, J. Med. Chem., 43, 3443 (2000); doi:10.1021/jm000164q.; (d) G.W. Bemis and M.A. Murcko, J. Med. Chem., 39, 2887 (1996); doi:10.1021/jm9602928.
  2. (a) A. Markham and K.L. Goa, Drugs, 54, 299 (1997); doi:10.2165/00003495-199754020-00009.; (b) K.F. Croom and G.M. Keating, Am. J. Cardiovasc. Drugs, 4, 395 (2004); doi:10.2165/00129784-200404060-00008.; (c) M. Sharpe, B. Jarvis and K.L. Goa, Drugs, 61, 1501 (2001); doi:10.2165/00003495-200161100-00009.; (d) S. Yusuf, Am. J. Cardiol., 89, 18 (2002); doi:10.1016/S0002-9149(01)02323-2.
  3. M.E. Matheron and M. Porchas, Plant Dis., 88, 665 (2004); doi:10.1094/PDIS.2004.88.6.665.
  4. (a) U. Schmidt, V. Leitenberger, H. Griesser, J. Schmidt and R. Meyer, Synthesis, 1248 (1992); doi:10.1055/s-1992-26351.; (b) U. Schmidt, R. Meyer, V. Leitenberger, H. Griesser and A. Lieberknecht, Synthesis, 1025 (1992); doi:10.1055/s-1992-26293.
  5. E. Poetsch, Kontakte, 2, 15 (1988).
  6. (a) N. Miyaura, K. Yamada and A. Suzuki, Tetrahedron Lett., 20, 3437 (1979); doi:10.1016/S0040-4039(01)95429-2.; (b) S.P. Stanforth, Tetrahedron, 54, 263 (1998); doi:10.1016/S0040-4020(97)10233-2.; (c) A. Suzuki, Pure Appl. Chem., 63, 419 (1991); doi:10.1351/pac199163030419.; (d) J.P. Wolfe and S.P. Buchwald, Angew. Chem. Int. Ed., 38, 2413 (1999); doi:10.1002/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO;2-H.; (e) A. Zapf and M. Beller, Chem. Eur J., 6, 1830 (2000); doi:10.1002/(SICI)1521-3765(20000515)6:10<1830::AID-CHEM1830>3.0.CO;2-8.; (f) R.B. Bedford, C.S.J. Cazin, S.J. Coles, T. Gelbrich, P.N. Horton, M.B. Hursthouse and M.E. Light, Organometallics, 22, 987 (2003); doi:10.1021/om020841+.
  7. (a) S. Baba and E. Negishi, J. Am. Chem. Soc., 98, 6729 (1976); doi:10.1021/ja00437a067.; (b) C. Dai and C. Fu, J. Am. Chem. Soc., 123, 2719 (2001); doi:10.1021/ja003954y.
  8. (a) K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972); doi:10.1021/ja00767a075.; (b) W.A. Herrmann, V.P.W. Bohm and C. Reisinger, J. Organomet. Chem., 576, 23 (1999); doi:10.1016/S0022-328X(98)01050-X.
  9. (a) Y. Hatanaka and T. Hiyama, J. Org. Chem., 53, 918 (1988); doi:10.1021/jo00239a056.; (b) K. Gouda, E. Hagiwara, Y. Hatanaka and T. Hiyama, J. Org. Chem., 61, 7232 (1996); doi:10.1021/jo9611172.; (c) M.E. Mowery and P. DeShong, Org. Lett., 1, 2137 (1999); doi:10.1021/ol991186d.; (d) J. Lee and G.C. Fu, J. Am. Chem. Soc., 125, 5616 (2003); doi:10.1021/ja0349352.; (e) S. Riggleman and P. Deshong, J. Org. Chem., 68, 8106 (2003); doi:10.1021/jo034809g.; (f) H.M. Lee and S.P. Nolan, Org. Lett., 2, 2053 (2000); doi:10.1021/ol005956t.
  10. (a) J.K. Stille, Pure Appl. Chem., 57, 1771 (1985); doi:10.1351/pac198557121771.; (b) J.K. Stille, Angew. Chem. Int. Ed. Engl., 25, 508 (1986); doi:10.1002/anie.198605081.; (c) V. Farina, V. Krishnamurthy and W. Scott, J. Org. React., 50, 1 (1997); (d) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz and M. Lemaire, Chem. Rev., 102, 1359 (2002); doi:10.1021/cr000664r.; (e) A.F. Littke and G.C. Fu, Angew. Chem. Int. Ed., 41, 4176 (2002); doi:10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U.
  11. (a) E. Hagiwara, K. Gouda, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 38, 439 (1997); doi:10.1016/S0040-4039(96)02320-9.; (b) M. Murata, R. Shimazaki, S. Watanabe and Y. Masuda, Synthesis, 2001, 2231 (2001); doi:10.1055/s-2001-18435.
  12. (a) C. Wolf and R. Lerebours, Org. Lett., 6, 1147 (2004); doi:10.1021/ol049851s.; (b) Á. Gordillo, E. de Jesús and C. López-Mardomingo, Org. Lett., 8, 3517 (2006); doi:10.1021/ol061221y.
  13. (a) S. Shi and Y. Zhang, J. Org. Chem., 72, 5927 (2007); doi:10.1021/jo070855v.; (b) B.C. Ranu, R. Dey and K. Chattopadhyay, Tetrahedron Lett., 49, 3430 (2008); doi:10.1016/j.tetlet.2008.03.121.; (c) T. Huang and C.J. Li, Tetrahedron Lett., 43, 403 (2002); doi:10.1016/S0040-4039(01)02193-1.; (d) D. Srimani, S. Sawoo and A. Sarkar, Org. Lett., 9, 3639 (2007); doi:10.1021/ol7015143.; (e) E. Alacid and C. Najera, Adv. Synth. Catal., 348, 945 (2006); doi:10.1002/adsc.200505494.; (f) E. Alacid and C. Najera, Adv. Synth. Catal., 348, 2085 (2006); doi:10.1002/adsc.200600262.
  14. A. Komaromi, F. Szabo and Z. Novak, Tetrahedron Lett., 51, 5411 (2010); doi:10.1016/j.tetlet.2010.07.170.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0