Water-soluble phosphines: Part XII. Pd catalyzed P-C coupling reactions: A novel synthetic route to cationic phosphines with para- and meta-guanidiniumphenyl moieties

Journal of Organometallic Chemistry

Volumn 602, Issue 1-2, 2000, Pages 158-169

  Machnitzki, Peter ^a   Tepper, Michael ^a   Wenz, Kirsten ^a   Stelzer, Othmar ^a   Herdtweck, Eberhardt ^b  

^a UNIVERSITY OF WUPPERTAL   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Ligand properties; Meta , para Guanidiniumphenyl phosphines; Pd catalyzed P C coupling; Suzuki coupling; X ray structure

Indexed keywords

LATEOLABRAX JAPONICUS;

EID: 0001010863     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00151-0     Document Type: Article

References (74)

1. D.J. Brauer, P. Machnitzki, T. Nickel, O. Stelzer, Eur. J. Inorg. Chem. (2000) 65.
2. (a) B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, vol. 2, VCH, Weinheim, 1996, p. 575.
3. (b) W.A. Herrmann, C.W. Kohlpaintner, Angew. Chem. 105 (1993) 1588; Angew. Chem. Int. Ed. Engl. 32 (1993) 1524.
4. (b) W.A. Herrmann, C.W. Kohlpaintner, Angew. Chem. 105 (1993) 1588; Angew. Chem. Int. Ed. Engl. 32 (1993) 1524.
5. Kuntz E. Chemtech. 17:1987;570.
6. (a) B. Mohr, D.M. Lynn, R.H. Grubbs, Organometallics 15 (1996) 4317.
7. (b) G. Peiffer, S. Chhan, A. Bendayan, B. Waegell, J.P. Zahra, J. Mol. Catal. 59 (1990) 1.
8. Smith R.T., Baird M.C. Inorg. Chim. Acta. 62:1982;135.
9. (a) A. Heßler, O. Stelzer, H. Dibowski, K. Worm, F.P. Schmidtchen, J. Org. Chem. 62 (1997) 2362.
10. (b) H. Dibowski, F.P. Schmidtchen, Angew. Chem. 110 (1998) 487; Angew. Chem. Int. Ed. Engl. 37 (1998) 476.
11. (b) H. Dibowski, F.P. Schmidtchen, Angew. Chem. 110 (1998) 487; Angew. Chem. Int. Ed. Engl. 37 (1998) 476.
12. (c) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. (1975) 4467.
13. (a)Y. Yamamoto, S. Kojima, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Amidines and Imidates, vol. 2, Wiley, New York, 1991, p. 485.
14. (b) M. Charton, J. Org. Chem. 30 (1965) 969.
15. (c) P.J. Taylor, A.R. Wait, J. Chem. Soc. Perkin Trans. 2 (1986) 1765.
16. (a) M.P. Fülscher, E.L. Mehler, J. Mol. Struct. (Theochem.) 165 (1988) 319.
17. (b) P.H. Boyle, A.P. Davis, K.J. Dempsey, G.D. Hosken, J. Chem. Soc. Chem. Commun. (1994) 1875.
18. (c) A. Gleich, F.P. Schmidtchen, Chem. Ber. 123 (1990) 907.
19. A. Heßler, M. Tepper, O. Stelzer, F.P. Schmidtchen, H. Dibowski, H. Bahrmann, M. Riedel (Hoechst AG), DE 197 01 245 (23/07/1998).
20. (a) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457.
21. (b) A. Suzuki, Pure Appl. Chem. 63 (1991) 419.
22. Herd O., Heßler A., Hingst M., Tepper M., Stelzer O. J. Organomet. Chem. 522:1996;69.
23. Herd O., Heßler A., Hingst M., Machnitzki P., Tepper M., Stelzer O. Catal. Today. 42:1998;413.
24. 31P-NMR-Spektroskopie, Thieme, Stuttgart, 1993.
25. (a) D.A. Baldwin, L. Denner, T.J. Egan, A.J. Markwell, Acta Crystallogr. Sect. C 42 (1986) 1197.
26. (b) J.M. Adams, R.W.H. Small, Acta Crystallogr. Sect. B 30 (1974) 2191.
27. (a) D.P. Burum, R.R.J. Ernst, J. Magn. Reson. 39 (1980) 163.
28. (b) M.R. Bendall, D.M. Doddrell, D.T. Peg, J. Am. Chem. Soc. 103 (1981) 4603.
29. 13C-NMR SpeKtroskopie, Thieme, Stuttgart, 1984, p. 199.
30. (b) K.T. Leffek, P. Pruszynski, K. Thanapaalasingham, Can. J. Chem. 67 (1989) 590.
31. Cameron D.G., Hudson H.R., Pianka M. Phosphorus. Sulfur Silicon. 83:1993;21.
32. Kanamori K., Roberts J.D. J. Am. Chem. Soc. 105:1983;4698.
33. Schomaker V., Stevenson D.P. J. Am. Chem. Soc. 63:1941;37.
34. Steward E.G., Warner D., Clarke G.R. Acta Crystallogr. Sect. B. 30:1974;813.
35. (a) C.L. Angell, N. Sheppard, A. Yamaguchi, T. Shimanouchi, T. Miyazawa, S. Mizushima, Trans. Faraday Soc. 53 (1957) 589.
36. (b) D.J. Haas, D.R. Harris, H.H. Mills, Acta Crystallogr. 19 (1965) 676.
37. (a) J.J. Daly, J. Chem. Soc. (A) (1964) 3799.
38. (b) B.J. Dunne, A.G. Orpen, Acta Crystallogr. Sect. C 47 (1991) 345.
39. (a) C.A. Tolman, W.C. Seidel, D.H. Gerlach, J. Am. Chem. Soc. 94 (1972) 2669.
40. (b) D.R. Coulson, Inorg. Synth. 13 (1972) 121.
41. (a) O. Herd, P. Machnitzki, K. Wenz, O. Stelzer, to be published.
42. (b) P. Machnitzki, T. Nickel, O. Stelzer, C. Landgrafe, Eur. J. Inorg. Chem. (1998) 1029.
43. (c) F. Bitterer, O. Herd, A. Heßler, M. Kühnel, K. Rettig, O. Stelzer, W.S. Sheldrick, S. Nagel, N. Rösch, Inorg. Chem. 35 (1996) 4103.
44. (a) R. Poilblanc, M. Bigorgne, Bull Soc. Chim. Fr. (1962) 1301.
45. (b) D.J. Darensbourg, C.J. Bischoff, Inorg. Chem. 32 (1993) 47.
46. (a) G. Charlot, B. Tremillon, Chemical Reactions in Solvents and Melts, Pergamon, Oxford, 1969, p. 274.
47. (b) E.A. Moelwyn-Hughes, Physical Chemistry, Pergamon, Oxford, 1961, pp. 301, 529.
48. (a) A.W. Verstuyft, J.H. Nelson, Inorg. Chem. 14 (1975) 1501.
49. (b) D.A. Redfield, J.H. Nelson, Inorg. Chem. 12 (1973) 15.
50. Balimann G., Motschi H., Pregosin P.S. Inorg. Chim. Acta. 23:1977;191.
51. Grim S.O., Keiter R.L. Inorg. Chim. Acta. 4:1970;56.
52. (a) T. Bartik, T. Himmler, J. Organomet. Chem. 293 (1985) 343.
53. (b) T. Bartik, B. Bartik, B.E. Hanson, I. Guo, I. Toth, Organometallics 12 (1993) 164.
54. (c) C. Larpent, H. Patin, Appl. Organomet. Chem. 1 (1987) 529.
55. Tolman C.A. Chem. Rev. 77:1977;313.
56. (a) O. Stelzer, E. Unger, Chem. Ber. 108 (1975) 1246.
57. (b) M.F. Lappert, J.B. Pedlley, B.T. Wilkins, O. Stelzer, E. Unger, J. Chem. Soc. Dalton Trans. (1975) 1207.
58. Bartik T., Himmler T., Schulte H.G., Seevogel K. J. Organomet. Chem. 272:1984;29.
59. (a) S. Haber, N. Egger (Hoechst AG), WO 97/05151 (13/02/1997).
60. (b) S. Haber, J. Manero (Hoechst AG), EP 694.530 (31/01/1996).
61. 2.
62. (a) W. Gee, R.A. Shaw, B.C. Smith, Inorg. Synth. 9 (1967) 19.
63. (b) F. Pass, H. Schindlbaur, Monatsh. Chem. 90 (1959) 148.
64. Crofts P.C. Kosolapoff G.M., Maier L. Organic Phosphorus Compounds. 6:1972;Wiley, New York.
65. Fehlhammer W.P., Herrmann W.A., Öfele K. Brauer G. third ed. Handbuch der Präparativen Anorganischen Chemie. III:1981;1799 Ferdinand Enke Verlag, Stuttgart.
66. (a) R. Pettit, J. Am. Chem. Soc. 81 (1959) 1266.
67. (b) M.A. Bennett, L. Pratt, G. Wilkinson, J. Chem. Soc. (1961) 2037.
68. (c) R.B. King, Inorg. Chem. 2 (1963) 936.
69. G.M. Sheldrick, SHELXL Program System, University of Göttingen, Germany, 1993.
70. A.J.C. Wilson (Ed.), International Tables for Crystallography, vol. C, Tables 6.1.1.4 (pp. 500-502), 4.2.6.8 (pp. 219-222), and 4.2.4.2 (pp. 193-199), Kluwer, Dordrecht, The Netherlands, 1992.
71. G. Artus, W. Scherer, T. Priermeier, E. Herdtweck, STRUX-V, A Program System to Handle X-ray Data, TU München, Germany, 1997.
72. A.L. Spek, PLATON-94-PLUTON-94, An Integrated Tool for the Analysis of the Results of a Single Crystal Structure Determination, Acta Crystallogr. Sect. A 46 (1990) C34.
73. G.M. Sheldrick, SHELXS-86, A Program for the Solution of Crystal Structures from Diffraction Data, Acta Crystallogr. Sect. A 46 (1990) 467.
74. G.M. Sheldrick, SHELXL-93, in: G.M. Sheldrick, C. Krüger, R. Goddard (Eds.), Crystallographic Computing 3, Oxford University Press, UK, 1993, pp. 175-189.