Synthesis and characterization of transition metal complexes of thiophene-2-methylamine: X-ray crystal structure of palladium (II) and platinum (II) complexes and use of palladium(II) complexes as pre-catalyst in Heck and Suzuki cross-coupling reactions

Applied Organometallic Chemistry

Volumn 23, Issue 11, 2009, Pages 467-475

  Aydemir, Murat ^a   Baysal, Akin ^a   Durap, Feyyaz ^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; Bis(phosphino)amine; Heck reaction; Palladium; Suzuki coupling

Indexed keywords

AMINOPHOSPHINE; BIS(PHOSPHINO)AMINE; CRYSTALLINE SOLIDS; ELEMENTAL ANALYSIS; H-NMR AND IR SPECTROSCOPY; HECK REACTION; PALLADIUM COMPLEXES; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; SUZUKI COUPLING; SUZUKI CROSS COUPLING REACTIONS; SYNTHESIS AND CHARACTERIZATION; X RAY CRYSTAL STRUCTURES;

AMINES; CATALYSIS; CATALYSTS; CRYSTAL STRUCTURE; METAL COMPLEXES; ORGANIC COMPOUNDS; PALLADIUM; PHOSPHORUS COMPOUNDS; PLATINUM; PLATINUM COMPOUNDS; SINGLE CRYSTALS; THIOPHENE; TRANSITION METAL COMPOUNDS; TRANSITION METALS; X RAY DIFFRACTION ANALYSIS;

PALLADIUM COMPOUNDS;

EID: 70350153780     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1547     Document Type: Article

References (93)

1. a) L. H. Pignolet, Homogeneous Catalysis with metal Phosphine Complexes. Plenum Press: New York, 1983, 137
2. b) P. W. N. M. Van Leeuwen, Organometallics 1997, 16, 3027
3. c) T. J. Kwok, D. J. Wink, Organometallics 1993, 12, 1954
4. d) H. Bricout, J. F. Carpentier, A. Mortreuz, Tetrahedron Lett. 1996, 37, 6105
5. e) I. Suisse, H. Bricout, A. Mortreux, Tetrahedron Lett. 1994, 35, 413
6. f) D. Gleich, R. Schmid, W. A. Herrmann, Organometallics 1998, 17, 2141
7. g) S. Ganguly, R. M. Roundhill, Organometallics 1993, 12, 4825
8. h) B. Cornils, E. G. Kuntz, J. Organomet. Chem. 1995, 502, 177.
9. a) M. S. Balakrishna, V. S. R. Reddy, S. S. Krishnamurthy, J. C. T. R. Burchkette St. Laurent, J. F. Nixon, Coord. Chem. Rev. 1994, 129, 1
10. b) J. T. Mague, J. Krinsky, Inorg. Chem. 2001, 40, 1962
11. c) A. M. Z. Slawin, M. B. Smith, J. D. Woollins, J. Chem. Soc. Rev. 1998, 1537
12. d) K. V. Katti, V. S. R. Reddy, P. R. Singh, Chem. Soc. Rev. 1995, 97
13. e) M. S. Balakrishna, P. P. George, S. M. Mobin, Polyhedron 2005, 24, 475.
14. a) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds. VCH: Basel, 1993, Vols 1 and 2
15. b) R. Noyori, Asymmetric Catalysis in Organic Synthesis. Wiley: New York, 1994
16. c) W. Keim, Angew. Chem., Int. Ed. Engl. 1990, 12, 251
17. d) W. Keim, Angew. Chem., Int. Ed. Engl. 1990, 29, 235
18. e) W. Keim, J. Mol. Cat.A:Chem. 1989, 52, 19
19. f) W. Reppe, N. V. Kutepow, A.Magin, Angew. Chem., Int. Ed. Engl. 1969, 81, 717
20. g) C. A. Tolman, J. Chem. Educ. 1986, 63, 199.
21. a) S. D. Ittel, C. A. Tolman, A. D. English, J. P. Jesson, J. Am. Chem. Soc. 1978, 100, 7577
22. b) J. W. Rathke, E. L. Muetterties, J. Am. Chem. Soc. 1975, 97, 3272
23. c) H. H. Karsch, H. F. Klein, H. Schmidbaur, Angew. Chem. Int. Ed. Engl. 1975, 14, 637
24. d) J. F. Hartwig, R. A. Anderson, R. G. Bergman, Organometallics 1991, 10, 1875
25. e) M. Antberg, L. Dahlenberg, Angew. Chem. Int. Ed. Engl. 1986, 25, 260
26. f) P. J. Desrosiers, R. S. Shinomoto, T. C. Flood, J. Am. Chem. Soc. 1986, 108, 1346
27. g) R. S. Shinomoto, P. J. Desrosiers, G. P. Harper, T. C. Flood, J. Am. Chem. Soc. 1988, 110, 7915.
28. J. F. Hartwig, R. A. Anderson, R.G. Bergman, Organometallics 1991, 10, 1710.
29. a) D. E. Fogg, B. R. James, Inorg. Chem. 1997, 36, 1961
30. b) A. M. Joshi, I. S. Thorburn, S. J. Rettig, B. R. James, Inorg. Chim. Acta 1992, 198, 283
31. c) P. R. Hoffman, K. G. Caulton, J. Am. Chem. Soc. 1975, 97, 4221
32. d) M. S. Balakrishna, R. Panda, D. C. Smith Jr., A. Klaman, S. P. Nolan, J. Organomet. Chem. 2000, 599, 159.
33. a) S. P. Stanforth, Tetrahedron 1998, 54, 263
34. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147.
35. A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. Engl. 2002, 41, 4176.
36. I. J. S. Fairlamb, S. Grant, A. C. Whitwood, J. Whitthall, A. S. Batsanov, J. C. Collings, J. Organomet. Chem. 2005, 690, 4462.
37. a) P. Loyd-Williams, E. Giralt, Chem. Soc. Rev. 2001, 30, 145
38. b) R. B. Bedford, Chem. Commun. 2003, 1787
39. c) C. Najera, J. Gil-Molto, S. Karlstr öm, L. R. Falvello, Org. Lett. 2003, 5, 1451.
40. N. Biricik, F. Durap, C. Kayan, B. G̈umg̈um, N. Gürb̈uz, I.özdemir, W. H. Ang, Z. Fei, R. Scopelliti, J. Organomet. Chem. 2008, 693, 2693.
41. H. H. Szmant, Organic Building Block of the Chemical Industry. Wiley: New York, 1989.
42. a) K. C. Nicolaou, H. Li, C. N. C. Body, J. M. Ramanjulu, T. Y. Yue, S. Natarajan, X. J. Chu, S. Brase, F. Rubsam, Chem. Eur. J. 1999, 5, 2584
43. b) K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622
44. c) K. Kamikawa, T. Watanabe, A. Daimon, M. Uemura, Tetrahedron 2000, 56, 2325.
45. a) V. V. Grushin, H. Alper, Top. Organomet. Chem. 1999, 3, 193
46. b) B. Punji, C. Ganesamoorthy, M. S. Balakrishna, J.Mol. Cat. 2006, 259, 78.
47. a) M. Aydemir, A. Baysal, B. G̈umg̈um, J. Organomet. Chem. 2008, 693, 3810
48. b) B. G̈umg̈um, N. Biricik, F. Durap, I.özdemir, N. Gürb̈uz, W. H. Ang, P. J. Dyson, Appl. Organometal. Chem. 2007, 21, 711
49. c) O. Akba., F. Durap, M. Aydemir, A. Baysal, B. G̈umg̈um, S.özkar, J. Organomet. Chem. 2009, 694, 731.
50. a) D. Drew, J. R. Doyle, Inorg. Synth. 1972, 13, 47
51. b) J. X. McDermott, J. F. White, G. M. Whitesides, J. Am. Chem. Soc. 1976, 98, 6521.
52. G. J. Kubas, Inorg. Synth. 1979, 19, 90.
53. G. Ewart, A. P. Lane, J. McKechnie, D. S. Payne, J. Chem. Soc. Sec A 1967, 1492.
54. A. Baysal,M. Aydemir, F. Durap, B. G̈umg̈um, S.özkar, L. T. Yíldírím, Polyhedron 2007, 26, 3373.
55. T. Appleby, S. M. Aucott, M. L. Clarke, A. M. Z. Slawin, J. D. Woollins, Polyhedron 2002, 21, 2639.
56. K. G. Gaw, M. B. Smith, J. W. Steed, J. Organomet. Chem. 2002, 664, 294.
57. a) M. R. I. Zubiri, H. I. Milton, A. M. Z. Slawin, J. D. Woollins, Inorg. Chim.Acta 2004, 357, 1243
58. b) N. Biricik, F. Durap, C. Kayan, N. Biricik, Heteroatom Chem. 2007, 18, 613.
59. a) K. G. Gaw, M. B. Smith, A. M. Z. Slawin, New J. Chem. 2000, 24, 429
60. b) E. J. Zijs, J. I. Van der Vlugt, D. M. Tooke, A. L. Spek, D. Vogt, J. Chem.Soc., DaltonTrans. 2005, 512
61. c) M. R. I. Zuburi,A. M. Z. Slawin, M. Wainwright, J. D. Woollins, Polyhedron 2002, 21, 1729
62. d) M. R. I. Zuburi, H. L.Milton, D. J. Cole-Hamilton, A. M. Z. Slawin, J. D. Woollins, Polyhedron 2004, 23, 693.
63. a) A. M. Z. Slawin, J. Wheatley, J. D. Woollins, Eur. J. Inorg. Chem. 2005, 713
64. b) Q. Zhang, G. Hua, P. Bhattacharyya, A. M. Z. Slawin, J. D. Woollins, J. Chem. Soc., Dalton Trans. 2003, 3250
65. c) M. R. I. Zuburi,H. L. Milton,A. M. Z. Slawin, J. D. Woollins, Polyhedron 2004, 23, 865
66. d) T. Q. Ly, A. M. Z. Slawin, J. D. Woollins, J. Chem. Soc., Dalton Trans. 1997, 1611
67. e) A. M. Z. Slawin, J. Wheatley, J. D. Woollins, Polyhedron 2004, 23, 2569.
68. a) F. Majoumo-Mbe, P. L önnecke, E. V. Novikova,G. P. Below, E. Hey- Hawkins, J. Chem. Soc., Dalton Trans. 2005, 3326
69. b) F. Durap, N. Biricik, B. G̈umg̈um, S. Özkar, W. A. Ang, Z. Fei, R. Scopelliti, Polyhedron 2008, 27, 196.
70. a) A. M. Z. Slawin, J. D. Woollins, Q. Zhang,J.Chem.Soc.,DaltonTrans. 2001, 621
71. b) M. S. Balakrishna, S. S. Krishnamurthy, R. Murugavel, M.Netaji, I. I. Mathews, J. Chem. Soc., Dalton Trans. 1993, 3, 477.
72. a) F. Majoumo, P. Lönnecke, O. Kühl, E. Hey-Hawkins, Z. Anorg. Allg. Chem. 2004, 630, 305
73. b) E. Lindler, M. Mohr, C. Nachtigal, R. Favzi, G. Henkel, J. Organomet. Chem. 2000, 595, 166.
74. a) A. M. Z. Slawin,H. L. Milton, J. Wheatley, J. D. Woollins, Polyhedron 2004, 23, 3125
75. b) A. M. Z. Slawin, J. Wheatley, J. D. Woollins, Phosphorus, Sulfur, Silicon Relat. Elem. 2004, 179(4-5), 991
76. c) M. Aydemir, A. Baysal, G.özẗurk, B. G̈umg̈um, Appl. Organometal. Chem. 2009, 23, 108
77. d) N. Biricik., F. Durap, B. G̈umg̈um, Z. Fei, R. Scopelliti, Trans. Met. Chem. 2007, 32, 877.
78. CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands, 1994.
79. XCAD4: K. Harms, & S. Wocadlo, XCAD4. University of Marburg, Germany, 1995.
80. G. M. Sheldrick, Acta Crystallogr. 2008, 64, 112.
81. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
82. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, & J. van de Streek, J. Appl. Crystallogr. 2006, 39, 453.
83. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
84. b) S. Kotha, K. Lahiri, D. Kashninath, Tetrahedron Lett. 2002, 9633.
85. L. Artok, H. Bulut, Tetrahedron Lett. 2004, 45, 3881.
86. I.özdemir, S. Yaşar, S. Demir, B. Çetinkaya, HeteroatomChem. 2005, 16(7), 557.
87. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2.
88. W. A. Herrmann, C. Brömer, K.öfele, C. Reisinger, T. Riermeier, M. Beller, H. Fischer, Angew. Chem., Int. Ed. Engl. 1995, 107, 1989.
89. A. L. Boyes, I. R. Butler, S. C. Quayle, TetrahedronLett. 1998, 39, 7763.
90. H. Brunner, N. Le Cousturier de Courey, J. P. Genet, Tetrahedron Lett. 1999, 40, 4815.
91. M. Beller, K. Kühlein, Synlett. 1995, 441.
92. F. Zhao, B. M. Bhanage, M. Shirai, M. Arai, J. Mol. Cat. A: Chem 1999, 142, 383.
93. E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, JohnWiley & Sons: New York, 2002, 1, 17.