Palladium(II) thiosemicarbazone-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl halides

Inorganic Chemistry Communications

Volumn 33, Issue , 2013, Pages 33-37

  Pandiarajan, Devaraj ^a   Ramesh, Rengan ^a   Liu, Yu ^b   Suresh, Rajamanickam ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

^b INSTITUTE OF HIGH ENERGY PHYSICS   (China)

Author keywords

Crystal structure; Palladium(II) pyridoxal thiosemicarbazone; Suzuki Miyaura cross coupling reaction

Indexed keywords

EID: 84877041936     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2013.03.032     Document Type: Article

References (49)

1. R.F. Heck Palladium Reagents in Organic Synthesis 1985 Academic Press New York
2. J.P. Collman, L.S. Hegedus, J.R. Norton, and R.G. Finke Principles and Applications of Organotransition Metal Chemistry 1987 University Science Mill Valley, CA
3. B.M. Trost, and T.R. Verhoven G. Wilkinson, F.G. Stone, E.W. Abel, Comprehensive Organometallic Chemistry 8 1982 Pergamon Oxford 799 938
4. A. Suzuki Cross-Coupling reactions of organoboranes: an easy way to construct C-C bonds Angew. Chem. Int. Ed. 50 2011 6722 6737
5. A. Suzuki, and Y. Yamamoto Cross-coupling reactions of organoboranes: an easy method for C-C bonding Chem. Lett. 40 2011 894 901
6. A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.M. Basset, and V. Polshettiwar Nanocatalysts for Suzuki cross-coupling reactions Chem. Soc. Rev. 40 2011 5181 5203
7. A. Balanta, C. Godard, and C. Claver Pd nanoparticles for C-C coupling reactions Chem. Soc. Rev. 40 2011 4973 4985
8. J.D. Sellars, and P.G. Steel Transition metal-catalysed cross-coupling reactions of P-activated enols Chem. Soc. Rev. 40 2011 5170 5180
9. G. Bringmann, C. Gunther, M. Ochse, O. Schupp, and S. Tasler W. Herz, H. Falk, G.W. Kirby, R.E. Moore, Progress in the Chemistry of Organic Natural Products 82 2001 Springer New York 1 293
10. K. Ding, and S. Wang Efficient synthesis of isoflavone analogues via a Suzuki coupling reaction Tetrahedron Lett. 46 2005 3707 3709
11. G.W. Kabalka, and B. Venkataiah The total synthesis of eupomatilones 2 and 5 Tetrahedron Lett. 46 2005 7325 7328
12. K.C. Nicolaou, C.N.C. Boddy, S. Brase, and N. Winssinger Chemistry, biology, and medicine of the glycopeptide antibiotics Angew. Chem. Int. Ed. 38 1999 2096 2152
13. H. Ban, M. Muraoka, and N. Ohashi Synthesis of SMP-797: a new potent ACAT inhibitor Tetrahedron 61 2005 10081 10092
14. P. Kumar, P.K. Pathak, V.K. Gupta, B.K. Srivastava, and B.S. Kushwaha Flurbiprofen and its derivatives of many therapeutic uses -a recent report Asian J. Chem. 16 2004 558 562
15. F.C. Krebs, and M. Jorgensen Controlling the energy levels of conducting polymers. Hydrogen versus fluorine in poly(dialkylterphenylenevinylene)s Macromolecules 35 2002 7200 7206
16. G.E. Collis, A.K. Burrell, and D.L. Officer β-Terthiophene aldehyde and phosphonate: key building blocks for the synthesis of functionalised conducting polymers Tetrahedron Lett. 42 2001 8733 8735
17. N. Miyaura, T. Yanagi, and A. Suzuki The palladium-catalyzed cross-coupling reaction of phenylboronic acid withhaloarenes in the presence of bases Synth. Commun. 11 1981 513
18. N. Miyaura, and A. Suzuki Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 95 1995 2457 2483
19. A. Suzuki Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles J. Organomet. Chem. 576 1999 147 168
20. S. Kotha, K. Lahiri, and D. Kashinath Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis Tetrahedron 58 2002 9633 9695
21. S. Darses, and J.P. Genet Potassium organotrifluoroborates: new perspectives in organic synthesis Chem. Rev. 108 2008 288 325
22. P.J. van Koningsbruggen, Y. Maeda, and H. Oshio Iron(III) spin crossover compounds Top. Curr. Chem. 233 2004 259 324
23. V.M. Leovac, V.S. Jevtovic, L.S. Jovanovic, and G.A. Bogdanovic J. Serb. Chem. Soc. 70 2005 393 422
24. L.S. Jovanovic, V.S. Jevtovic, V.M. Leovac, and L.J. Bjelica J. Serb. Chem. Soc. 70 2005 187 200
25. W.A. Herrmann, V.P.W. Bohm, and C.P. Reisinger Application of palladacycles in Heck type reactions J. Organomet. Chem. 576 1999 23 41
26. J. Dupont, M. Pfeffer, and J. Spencer Palladacycles -an old organometallic family revisited: new, simple, and efficient catalyst precursors for homogeneous catalysis Eur. J. Inorg. Chem. 2001 1917 1927
27. M. Beller, H. Fischer, W.A. Hermann, K. Ofele, and C. Brossmer Palladacycles as efficient catalysts for aryl coupling reactions Angew. Chem. Int. Ed. 34 1995 1848
28. D.A. Albisson, R.B. Bedford, S.E. Lawrence, and P.N. Scully Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions Chem. Commun. 1998 2095 2096
29. S. Gibson, D.F. Foster, G.R. Eastham, R.P. Tooze, and D. Cole-Hamilton Highly efficient C-C coupling reactions usingmetallated benzylphosphine complexes of palladium J. Chem. Commun. 2001 779 780
30. R.B. Bedford, and S.L. Welch Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reaction Chem. Commun. 2001 129 130
31. C.M. Zhang, and M.L. Trudell Palladium-bisimidazol-2-ylidene complexes as catalysts for general and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids Tetrahedron Lett. 41 2000 595 598
32. D.S. McGuinness, and K.J. Cavell Donor-functionalized heterocyclic carbene complexes of palladium(ii): efficient catalysts for C-C coupling reactions Organometallics 19 2000 741 748
33. G.R. Rosa, G. Ebeling, J. Dupont, and A.L. Monteiro A superior non-symmetrical NCP pincer type palladacycle catalyst precursor for the coupling of aryl boronic acids with aryl chlorides Synthesis 18 2003 2894 2897
34. B. Ines, R. SanMartin, F. Churruca, E. Dominquez, M.K. Urtiga, and M.I. Arriortua A nonsymmetric pincer-type palladium catalyst in Suzuki, Sonogashira, and Hiyama couplings in neat water Organometallics 27 2008 2833 2839
35. J.L. Bolliger, O. Blacque, and C.M. Frech Short, facile, and high-yielding synthesis of extremely efficient pincer-type Suzuki catalysts bearing aminophosphine substituents Angew. Chem. Int. Ed. 46 2007 6514 6517
36. 5)]}OTf Eur. J. Inorg. Chem. 2008 572 576
37. P. Pelagatti, A. Venturini, A. Leporat, M. Carcelli, M. Costa, A. Bacchi, G. Pelizzi, and C. Pelizzi Chemoselective homogeneous hydrogenation of phenylacetylene using thiosemicarbazone and thiobenzoylhydrazone palladium(II) complexes as catalysts J. Chem. Soc. Dalton Trans. 1998 2715 2721
38. I.D. Kostas, B.R. Steele, A. Terzis, S.V. Amosova, A.V. Martynov, and N.A. Makhaeva New palladium complexes with S-or Se-containing Schiff-base ligands as efficient catalysts for the Suzuki-Miyaura cross-coupling reaction of aryl bromides with phenylboronic acid under aerobic conditions Eur. J. Inorg. Chem. 2006 2642 2646
39. D.H. Lee, J.Y. Jung, I.M. Lee, and M.J. Jin (β-Oxoiminato) (phosphanyl)palladium complexes as highly active catalysts in Suzuki Miyaura coupling reactions Eur. J. Org. Chem. 2008 356 360
40. I.D. Kostas, F.J. Andreadaki, D.K. Demertzi, C. Prentjas, and M.A. Demertzis Suzuki-Miyaura cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under aerobic conditions catalyzed by palladium complexes with thiosemicarbazone ligands Tetrahedron Lett. 46 2005 1967 1970
41. D.M. Demertzi, N. Kourkoumelis, K. Derlat, J. Michalak, F.J. Andreadaki, and I.D. Kostac Thiosemicarbazone-derivatised palladium nanoparticles as efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides with phenylboronic acid Inorg. Chim. Acta 361 2008 1562 1565
42. P. Paul, S. Datta, S. Halder, R. Acharyya, F. Basuli, R.J. Butcher, S.M. Peng, G.H. Lee, A. Castineiras, M.G.B. Drew, and S. Bhattacharya Syntheses, structures and efficient catalysis for C-C coupling of some benzaldehyde thiosemicarbazone complexes of palladium J. Mol. Catal. A Chem. 344 2011 62 73
43. M.U. Raja, and R. Ramesh New binuclear Pd(II) thioamide complexes for the Heck reaction of aryl bromides Tetrahedron Lett. 52 2011 5427 5430
44. D. Pandiarajan, and R. Ramesh Suzuki-Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes J. Organomet. Chem. 708-709 2012 18 24
45. E. Sindhuja, R. Ramesh, and Y. Liu Palladium(II) thiocarboxamide complexes: synthesis, characterisation and application to catalytic Suzuki coupling reactions Dalton Trans. 41 2012 5351 5361
46. 2O Inorg. Chim. Acta 236 1995 83 88
47. 2] Inorg. Chim. Acta 236 1995 101 108
48. R. Raveendran, and S. Pal Polyhedron 27 2008 655
49. A. Bele, R. Ballesteros, F. Blanco, A. Bouillon, V. Collot, J. Dominguez, J. Lancelot, and S. Rault Synthesis of novel triazolopyridylboronic acids and esters. Study of potential application to Suzuki-type reactions Tetrahedron 60 2004 488