Synthesis and characterization of new bis(diphenylphosphino)aniline ligands and their complexes: X-ray crystal structure of palladium(II) and platinum(II) complexes, and application of palladium(II) complexes as pre-catalysts in Heck and Suzuki cross-coupling reactions

Polyhedron

Volumn 28, Issue 12, 2009, Pages 2313-2320

  Aydemir, Murat ^a   Durap, Feyyaz ^a   Baysal, Akin ^a   Akba, Osman ^a   Gümgüm, Bahattin ^a   Özkar, Saim ^b   Yildirim, Leyla Tatar ^c  

^a DICLE UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^c HACETTEPE UNIVERSITY   (Turkey)

Author keywords

Aminophosphine; Catalysis; Complexes; Crystal structures; Heck reaction; Suzuki coupling

Indexed keywords

CATALYST ACTIVITY; CHELATION; COORDINATION REACTIONS; COPPER COMPOUNDS; CRYSTAL ATOMIC STRUCTURE; INDIUM COMPOUNDS; METAL IONS; PALLADIUM COMPOUNDS; PLATINUM COMPOUNDS; SELENIUM COMPOUNDS; SINGLE CRYSTALS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

AMINOPHOSPHINES; CARBON ATOMS; COMPLEX; CRYSTALS STRUCTURES; HECK REACTIONS; PRECATALYSTS; SUZUKI COUPLINGS; SUZUKI CROSS COUPLING REACTIONS; SYNTHESIS AND CHARACTERIZATIONS; X RAY CRYSTAL STRUCTURES;

ANILINE;

EID: 67650168098     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.poly.2009.04.033     Document Type: Article

References (72)

1. Appleby T., and Woollins J.D. Coord. Chem. Rev. 235 (2002) 121
2. Bhattacharrya P., and Woollins J.D. Polyhedron 14 (1995) 3367
3. Fey N., Harvey J.N., Lloyd-Jones G.C., Murray P., Orpen A.G., Osborne R., and Purdie M. Organometallics 27 (2008) 1372
4. Majoumo-Mbe F., Lönnecke P., Novikova E.V., Belov G.P., and Hey-Hawkins E. J. Chem. Soc., Dalton Trans. (2005) 3326
5. Bourghida M., and Widhalm M. Tetrahedron: Asymmetry 9 (1998) 1073
6. Wang Y., Guo H., and Ding K.L. Tetrahedron: Asymmetry 11 20 (2000) 4153
7. Wang Y., Li X., and Ding K.L. Tetrahedron Lett. 43 (2002) 159
8. Mino T., Tanaka Y., Yabusaki Y., Okumara D., Sakamoto M., and Fujita T. Tetrahedron: Asymmetry 14 (2003) 2503
9. Urgaonkar S., and Verkade J.G. Tetrahedron 60 (2004) 11837
10. Urgaonkar S., and Verkande J.G. Adv. Synth. Catal. 346 (2004) 611
11. Parisel S.L., Adrio L.A., Pereira A.A., Perez M.M., Vila J.M., and Hii K.K. Tetrahedron 61 (2005) 9822
12. Reetz M.T., Lohmer G., and Schwickardi R. Angew. Chem., Int. Ed. Engl. 36 (1997) 1526
13. Reddy K.R., Surekha K., Lee G.H., Peng S.M., and Lui S.T. Organometallics 19 13 (2000) 2637
14. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 8 (2000) 3009
15. Mansour A., and Portnony M. Tetrahedron Lett. 44 (2003) 2195
16. Catsoulacos D.P., Steele B.R., Heropoulos G.A., Micha-Screttas M., and Screttas C.G. Tetrahedron Lett. 44 (2003) 4575
17. Hou X.-L., Dong D.X., and Yuan K. Tetrahedron: Asymmetry 15 (2004) 2189
18. Zotto D.L., Zangrando E., Baratta W., Felluga A., Martinuzzi P., and Rigo P. Eur. J. Inorg. Chem. (2005) 4707
19. Akba O., Durap F., Aydemir M., Baysal A., Gümgüm B., and Özkar S. J. Organomet. Chem. 694 5 (2009) 731
20. Aydemir M., Baysal A., Öztürk G., and Gümgüm B. Appl. Organomet. Chem. 23 (2009) 108
21. Clarke M.L., Cole-Hamilton D.J., and Woollins J.D. J. Chem. Soc., Dalton Trans. (2001) 2721
22. Schareina T., and Kepme R. Angew. Chem., Int. Ed. Engl. 41 (2002) 1521
23. Urgaonkar S., Nagarajan M., and Verkade J.G. Tetrahedron Lett. 43 (2002) 8921
24. Cheng J., Wang F., Xu J.-H., Pan Y., and Zhang Z. Tetrahedron Lett. 44 (2003) 7095
25. Bellina F., Carpita A., and Rossi R. Synthesis 15 (2004) 2419
26. Abu-Gnim C., and Amer I. J. Organomet. Chem. 516 (1996) 235
27. Saluzzo C., Breuzard J., Pellet-Rostaing S., Vallet M., Guyader F.L., and Lemaire M. J. Organomet. Chem. 643 (2002) 98
28. Andriev J., Richard P., Camus J.M., and Poli R. Inorg. Chem. 41 5 (2002) 3876
29. Zijp E.J., Van der Vlugt J.I., Tooke D.M., Spek A.L., and Vogt D. J. Chem. Soc., Dalton Trans. 3 (2005) 512
30. Guo R.W., Lough A.J., Morris R.H., and Song D.T. Organometallics 23 23 (2004) 5524
31. Blanc C., Agbossou-Niedercorn F., and Nowogrocki G. Tetrahedron: Asymmetry 15 (2004) 2159
32. Xing Y., Chen J.S., Dong Z.R., Li Y.Y., and Gas J.X. Tetrahedron Lett. 47 (2006) 4501
33. Pugin B., and Blaser H.U. Adv. Synth. Catal. 348 (2006) 1743
34. Demir S., Özdemir I., and Çetinkaya B. Appl. Organomet. Chem. 20 (2006) 254
35. Özdemir I., Yiǧit M., Çetinkaya E., and Çetinkaya B. Appl. Organomet. Chem. 20 (2006) 187
36. Punji B., Ganesamoorthy G., and Balakrishna M.S. J. Mol. Catal. A 259 (2006) 78
37. Bedford R.B., and Welch S.L. Chem. Commun. (2001) 129
38. Hartley F.R. The Chemistry of Organophosphorus Compounds (1990), Wiley, Manchester p. 1
39. Greenwood N.N., and Earnshaw A. Chemistry of Elements (1984), Pergamon Press, Oxford p. 619
40. Balakrishna M.S., Panda R., Smith Jr. D.C., Kalamn A., and Nolan S.P. J. Organomet. Chem. 599 (2000) 159
41. Bollmann A., Blann K., Dixon J.T., Hess F.M., Killian E., Maumela H., McGuinness D.S., Morgan D.H., Nevelling A., Otto S., Overett M., Slawin A.M.Z., Wasserscheid P., and Kuhlmann S. JACS 126 (2004) 14712
42. Bawen L.E., and Wass D.F. Organometallics 25 (2006) 555
43. Jabri A., Crewdson P., Gambarotta S., Korobkov I., and Duchateav R. Organometallics 25 (2006) 715
44. Teo S., Weng Z., and Hor T.S.A. Organometallics 27 (2008) 4188
45. Balakrishna M.S., Ramaswamy K., and Abhyankar R.M. J. Organomet. Chem. 560 (1998) 131
46. Gaw K.G., Smith M.B., and Slawin A.M.Z. New J. Chem. 24 (2000) 429
47. Biricik N., Durap F., Gumgum B., Fei Z., and Scopelliti R. Transition Met. Chem. 32 7 (2007) 877
48. Necas M., Foreman M.R.J., Marek J., Woollins J.D., and Novosad J. New J. Chem. 25 (2001) 1256
49. Killian E., Blann K., Bollmann A., Dixon J.T., Kuhlmann S., Mavmela M.C., Maumela H., Morgan D.H., Nongodlwana P., Overett M.J., Pretorius M., Höfener K., and Wasserscheid P. J. Mol. Catal. A 270 (2008) 214
50. Aydemir M., Baysal A., and Gümgüm B. J. Organomet. Chem. 693 (2008) 3810
51. Biricik N., Durap F., Kayan C., and Gümgüm B. Heteroatom Chem. 18 6 (2007) 613
52. Fei Z., Neda I., Thönnessen H., Jones P.G., and Schmutzler R. Phosphorus, Sulfur, Silicon Relat. Elem. 131 (1997) 1
53. Fei Z., Thönnessen H., Jones P.G., and Schmutzler R. Z. Anorg. Allg. Chem. 625 (1999) 1732
54. Fei Z., Lu Y., Freytag M., Jones P.G., and Schmutzler R. Z. Anorg. Allg. Chem. 626 (2000) 969
55. Biricik N., Durap F., Kayan C., Gümgüm B., Gürbüz N., Özdemir I., Ang W.H., Fei Z., and Scopelliti R. J. Organomet. Chem. 693 (2008) 2693
56. Milton H.L., Wheatley M.V., Slawin A.M.Z., and Woollins J.D. Inorg. Chem. Commun. 7 10 (2004) 1106
57. Fei Z., Ang W.H., Zhao D., Scopelliti R., and Dyson P.J. Inorg. Chim. Acta 359 (2006) 2635
58. Durap F., Biricik N., Gümgüm B., Özkar S., Ang W.H., Fei Z., and Scopelliti R. Polyhedron 27 (2008) 196
59. Slawin A.M.Z., Woollins J.D., and Zhang Q. J. Chem. Soc., Dalton Trans. (2001) 621
60. Slawin A.M.Z., Milton H.L., Wheatley J., and Woollins J.D. Polyhedron 23 (2004) 3125
61. Slawin A.M.Z., Wheatley J., and Woollins J.D. Phosphorus, Sulfur, Silicon Relat. Elem. 179 4-5 (2004) 991
62. Nardelli M. J. Appl. Cryst. 28 (1995) 659
63. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. Engl. 41 (2002) 4176
64. Gümgüm B., Biricik N., Durap F., Özdemir I., Gürbüz N., Ang W.H., and Dyson P.J. Appl. Organomet. Chem. 21 (2007) 711
65. Özdemir I., Yaşar S., Demir S., and Çetinkaya B. Heteroatom Chem. 16 7 (2005) 557
66. Drew D., and Doyle J.R. Inorg. Synth. 13 (1972) 47
67. McDermott J.X., White J.F., and Whitesides G.M. J. Am. Chem. Soc. 98 (1976) 6521
68. Kubas G.J. Inorg. Synth. 19 (1979) 90
69. cad-4 Express Software, Version 1.1, Enraf-Nonius, Delft, The Netherlands, 1993.
70. K. Horms, S. Wocadlo, xcad-4, Program for Processing cad-4 Diffractometer Data, University of Marburg, Germany, 1995.
71. G.M. Sheldrick, shelxs97 and shelxl97, Program for Crystal Structure Sulution and Refinement, University of Göttingen, Germany, 1997.
72. Farrugia L.J. J. Appl. Cryst. 30 (1997) 565