Regioselective cyclometallation of 4-R-1-naphthaldehyde benzoylhydrazones: Palladium(II) complexes with CNO pincer like ligands

Journal of Organometallic Chemistry

Volumn 731, Issue , 2013, Pages 67-72

  Rao, A R Balavardhana ^a   Pal, Samudranil ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Benzoylhydrazone; Crystal structure; Cyclopalladation; Palladium(II); Peri metallation

Indexed keywords

AMIDE FUNCTIONALITIES; BENZOYLHYDRAZONE; CYCLOPALLADATED COMPLEXES; CYCLOPALLADATION; GENERAL FORMULAS; PALLADIUM COMPLEXES; PERI-METALLATION; TRIDENTATE LIGANDS;

ACETONE; CHLORINE COMPOUNDS; COMPLEXATION; CRYSTAL STRUCTURE; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; PALLADIUM; REGIOSELECTIVITY; X RAY CRYSTALLOGRAPHY;

PALLADIUM COMPOUNDS;

INSECTIVORA;

EID: 84874929244     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.02.007     Document Type: Article

References (71)

1. M.P. Munoz, B. Martin-Matute, C. Fernandez-Rivas, D.J. Cardenas, and A.M. Echavarren Adv. Synth. Catal. 343 2001 338 342
2. A. Schnyder, A.F. Indolese, M. Studer, and H.-U. Blaser Angew. Chem. Int. Ed. 41 2002 3668 3671
3. J. Bravo, C. Cativiela, R. Navarro, and E.P. Urriolabeitia J. Organomet. Chem. 650 2002 157 172
4. C.S. Consorti, M.L. Zanini, S. Leal, G. Ebeling, and J. Duport Org. Lett. 5 2003 983 986
5. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527 2572
6. J. Spencer, D.P. Sharratt, J. Duport, A.L. Monteiro, V.I. Reis, M.P. Stracke, F. Rominger, and I.M. McDonald Organometallics 24 2005 5665 5672
7. A.D. Raybov Synthesis 1985 233 252
8. D.C.R. Hockless, R.C. Mayadunne, and B. Wild Tetrahedron: Asymmetry 6 1995 3031 3037
9. L.E. Overman, and T.P. Remarchuk J. Am. Chem. Soc. 124 2002 12 13
10. B.J. Burke, and L.E. Overman J. Am. Chem. Soc. 126 2004 16820 16833
11. I. Aiello, D. Dattilo, M. Ghedini, A. Bruno, R. Termine, and A. Golemme Adv. Mater. 14 2002 1233 1236
12. B.W. D'Andrade, J. Books, V. Adamovich, M.E. Thompson, and S.R. Forrest Adv. Mater. 14 2002 1032 1036
13. R.C. Evans, P. Douglas, and C.J. Winscom Coord. Chem. Rev. 250 2006 2093 2126
14. J. Kalinowski, V. Fattori, M. Cocchi, and J.A.G. Williams Coord. Chem. Rev. 255 2011 2401 2425
15. I. Omae Chem. Rev. 79 1979 287 321
16. A.D. Ryabov Chem. Rev. 90 1990 403 424
17. I. Omae Coord. Chem. Rev. 248 2004 995 1023
18. M. Ghedini, I. Aiello, A. Crispini, A. Golemme, M.L. Deda, and D. Pucci Coord. Chem. Rev. 250 2006 1373 1390
19. J. Dupont, and M. Pfeffer Palladacycles: Synthesis, Characterization and Applications 2008 Wiley-VCH Weinheim
20. C.H. Jun, J.B. Hong, Y.H. Kim, and K.Y. Chung Angew. Chem. Int. Ed. 39 2000 3440 3442
21. Y.G. Lim, J.S. Han, B.T. Koo, and J.B. Kang J. Mol. Catal. A: Chem. 209 2004 41 49
22. E.J. Yoo, M. Wasa, and J.Q. Yu J. Am. Chem. Soc. 132 2010 17378 17380
23. C. Zhu, W. Xie, and J.R. Falck Chem. Eur. J. 17 2011 12591 12595
24. M. Albrecht, and G. van Koten Angew. Chem. Int. Ed. 40 2001 3750 3781
25. D. Morales-Morales, and C.M. Jensen The Chemistry of Pincer Compounds 2007 Elsevier Amsterdam
26. W. Leis, H.A. Mayer, and W.C. Kaska Coord. Chem. Rev. 252 2008 1787 1797
27. N. Selander, and K.J. Szabó Chem. Rev. 111 2011 2048 2076
28. J.-L. Niu, X.-Q. Hao, J.-F. Gong, and M.-P. Song Dalton Trans. 40 2011 5135 5150
29. G. van Koten Organometallic Pincer Chemistry D. Milstein Topics in Organometallic Chemistry vol. 40 2013 Springer Heidelberg
30. C.S. Consorti, G. Ebeling, F. Rodembusch, V. Stefani, P.R. Livotto, F. Rominger, F.H. Quina, C. Yihwa, and J. Dupont Inorg. Chem. 43 2004 530 536
31. C.S. Consorti, G. Ebeling, F.R. Flores, F. Rominger, and J. Dupont Adv. Synth. Catal. 346 2004 617 624
32. J. Vicente, J.-A. Abad, J. López-Serrano, P.G. Jones, C. Nájera, and L. Botella-Sergura Organometallics 24 2005 5044 5057
33. J. Storch, J. Čermák, M. Pošta, J. Sýkora, and I. Císařová J. Organomet. Chem. 693 2008 3029 3034
34. B. Vabre, Y. Canac, C. Duhayon, R. Chauvin, and D. Zargarian Chem. Commun. 48 2012 10446 10448
35. G.R. Rosa, and D.S. Rosa RSC Adv. 2 2012 5080 5083
36. S. Das, and S. Pal J. Organomet. Chem. 689 2004 352 360
37. S. Das, and S. Pal J. Organomet. Chem. 691 2006 2575 2583
38. R. Raveendran, and S. Pal J. Organomet. Chem. 692 2007 824 830
39. R. Raveendran, and S. Pal J. Organomet. Chem. 694 2009 1482 1486
40. A.R.B. Rao, and S. Pal J. Organomet. Chem. 696 2011 2660 2664
41. A.R.B. Rao, and S. Pal J. Organomet. Chem. 701 2012 62 67
42. J. Granell, R. Moragas, J. Sales, M. Font-Bardía, and X. Solans J. Chem. Soc., Dalton Trans. 1993 1237 1244
43. Y.-F. Han, H. Li, P. Hu, and G.-X. Jin Organometallics 30 2011 905 911
44. A.J. Klaus, and P. Rys Helv. Chim. Acta 64 1981 1452 1466
45. M. Hugentobler, A.J. Klaus, H. Mettler, P. Rys, and G. Wehrle Helv. Chim. Acta 65 1982 1202 1211
46. R. Annunziata, S. Cenini, F. Demartin, G. Palmisano, and S. Tollari J. Organomet. Chem. 496 1995 C1 C3
47. M. Crespo, M. Font-Bardía, S. Pérez, and X. Solans J. Organomet. Chem. 642 2002 171 178
48. Y. Li, K.-H. Ng, S. Selvaratnam, G.-K. Tan, J.J. Vittal, and P.-H. Leung Organometallics 22 2003 834 842
49. R. Bhawmick, P. Das, D.N. Neogi, and P. Bandyopadyay Polyhedron 25 2006 1177 1181
50. L. Kind, A.J. Klaus, P. Rys, and V. Gramlich Helv. Chim. Acta 81 1998 307 316
51. S. Lentijo, J.A. Miguel, and P. Espinet Organometallics 30 2011 1059 1066
52. S. Lentijo, J.A. Miguel, and P. Espinet Dalton Trans. 40 2011 7602 7609
53. S. Tollari, G. Palmisano, F. Dematrin, M. Grassi, S. Magnaghi, and S. Cenini J. Organomet. Chem. 488 1995 79 83
54. M. Crespo, and E. Evangelio J. Organomet. Chem. 689 2004 1956 1964
55. D.N. Neogi, P. Das, A.N. Biswas, and P. Bandyopadhyay Polyhedron 25 2006 2149 2152
56. D.N. Neogi, A.N. Biswas, P. Das, R. Bhawmick, and P. Bandyopadhyay Inorg. Chim. Acta 360 2007 2181 2186
57. A.N. Biswas, P. Das, V. Bagchi, A. Choudhury, and P. Bandyopadhyay Eur. J. Inorg. Chem. 2011 3739 3748
58. A.N. Biswas, P. Das, S. Sengupta, A. Choudhury, and P. Bandyopadhyay RSC Adv. 1 2011 1279 1286
59. D.N. Neogi, A.N. Biswas, P. Das, R. Bhawmick, and P. Bandyopadhyay J. Organomet. Chem. 724 2013 147 154
60. D.D. Perrin, W.L.F. Armarego, and D.P. Perrin Purification of Laboratory Chemicals second ed. 1983 Pergamon Oxford
61. SMART Version 5.630 and SAINT-plus Version 6.45 2003 Bruker-Nonius Analytical X-ray Systems Inc. Madison, WI, USA
62. G.M. Sheldrick SADABS, Program for Area Detector Absorption Correction 1997 University of Göttingen Göttingen, Germany
63. CrysAlisPro Version 1.171.33.55 2007 Oxford Diffraction Ltd. Abingdon, Oxfordshire, UK
64. G.M. Sheldrick XHELX-97, Structure Determination Software 1997 University of Göttingen Göttingen, Germany
65. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837 838
66. A.L. Spek Platon, A Multipurpose Crystallographic Tool 2002 Utrecht University Utrecht, The Netherlands
67. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P.A. Wood J. Appl. Crystallogr. 41 2008 466 470
68. J.M. Dixon, M. Taniguchi, and J.S. Lindsey Photochem. Photobiol. 81 2005 212 213
69. S. Suzuki, T. Fuji, and T. Ishikawa J. Mol. Spectrosc. 57 1975 490 499
70. L. Cuffe, R.D.A. Hudson, J.F. Gallagher, S. Jennings, C.J. McAdam, R.B.T. Connelly, A.R. Manning, B.H. Robinson, and J. Simpson Organometallics 24 2005 2051 2060
71. Y.-Y. Liu, M. Grzywa, M. Tonigold, G. Sastre, T. Schüttrigkeit, N.S. Leeson, and D. Volkmer Dalton Trans. 40 2011 5926 5938