Synthesis and characterization of N-heterocyclic carbene phospha-palladacycles and their properties in Heck catalysis

Organometallics

Volumn 24, Issue 18, 2005, Pages 4416-4426

  Frey, Guido D ^a   Schütz, Jan ^a   Herdtweck, Eberhardt ^a   Herrmann, Wolfgang A ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHARACTERIZATION; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ARYL CHLORIDES; CARBENES; HECK CATALYSIS;

OLEFINS;

EID: 24944508573     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049001g     Document Type: Article

References (91)

1. (a) Mizoroki, T.; Mon, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
3. (a) Heck, R. F., Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis, Bd. 4; Pergamon: Oxford, 1991; Chapter 4.3, p 833.
4. (b) de Meijere, A.; Meyer, F. E. Angew. Chem. 1995, 106, 2473;
5. Angew. Chem., Int. Ed. Engl. 1995, 33, 2379.
6. (c) Cabri, W.; Caudiani, I. Acc. Chem. Res. 1995, 28, 2.
7. (a) Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, D. Organometallics 1992, 11, 1995.
8. (b) Bozell, J. J.; Vogt, C. E. J. Am. Chem. Soc. 1988, 110, 2655.
9. (c) Spencer, A. J. Organomet. Chem. 1984, 270, 115.
10. (d) Alper, H.; Grushin, V. V. Chem. Rev. 1994, 94, 1047.
11. (a) Cheney, A. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1972, 754.
12. (b) Shaw, B. L. New J. Chem. 1998, 77.
13. (c) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.
14. Gainsford, G. J.; Mason, R. J. Organomet. Chem. 1974, 80, 395.
15. (a) Alyea, E. C.; Dias, S. A.; Ferguson, G.; Roberts, P. J. J. Chem. Soc., Dalton Trans. 1979, 948.
16. (b) Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188.
17. Mitsudo, T.; Fischetti, W.; Heck, R. F. J. Org. Chem. 1984, 49, 1640.
18. (a) Herrmann, W. A.; Brossmer, C.; Öfele, K; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 207,1989;
19. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
20. (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
21. (c) Herrmann, W. A.; Böhm, V. P. W. J. Organomet. Chem. 1999, 572, 141.
22. (d) Böhm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017.
23. (e) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem. 1995, 107, 1992;
24. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
25. (f) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A 1996, 108, 51.
26. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073.
27. (h) Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23.
28. (i) Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Chem. Ed. 2000, 77, 92.
29. (j) Böhm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2001, 7, 4191.
30. (k) Herrmann, W. A.; Öfele, K.; v. Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229.
31. Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917.
32. Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283.
33. Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
34. Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793.
35. (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095.
36. (b) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. 2002, 114, 4294;
37. Angew. Chem., Int. Ed. 2002, 41, 4120.
38. (c) Bedford, R. B. Chem. Commun. 2003, 1787.
39. (d) Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Hursthouse, M. B.; Scordia, V. J. M. J. Chem. Soc., Dalton Trans. 2003, 3350.
40. (e) Bedford, R. B.; Hazelwood, S. L.; Horton, P. N.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2003, 4164.
41. For reviews see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 8, 1290.
42. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12.
43. (c) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2001, 48, 1.
44. (d) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181.
45. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
46. (f) Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
47. (a) Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
48. (b) Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. J. Org. Lett. 2003, 5, 1479.
49. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
50. Reisinger, C.-P. Ph.D. Thesis, Technische Universität München, 1997, ISBN 3-933083-00-1.
51. (a) Frey, G. D.; Reisinger, C.-P.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2005, 690, 3193.
52. (b) Frey, G. D.; Herdtweck, E.; Hermann, W. A. Abstracts of Papers, 229th ACS National Meeting 2005, San Diego, CA, March 13-17, 2005; INOR 616.
53. (a) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2000, 617-618, 616.
54. (b) Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2001, 21, 700.
55. (c) Gstöttmayr, C. W. K; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. 2002, 114, 1421;
56. Angew. Chem., Int. Ed. 2002, 41, 1363.
57. (d) Gstöttmayr, C. W. K. Ph.D. Thesis, Technische Universität München, 2002, ISBN 3-934767-61-3.
58. (e) Buron, C.; Stelzig, L.; Guerret, O.; Gornitzka, H.; Romanenko, V.; Bertrand, G. J. Organomet. Chem. 2002, 664, 70.
59. (f) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70.
60. (g) Enders, D.; Gielen, H.; Raabe, G.; Runsink, J.; Teles, J. H. Chem. Ber. 1996, 129, 1483.
61. (a) Schwarz, J. Ph.D. Thesis, Technische Universität München, 2000, ISBN 3-89791-111-6.
62. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773.
63. Clark, G. R.; Orbell, J. D. J. Organomet. Chem. 1981, 215, 121.
64. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
65. (b) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
66. (a) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1988.
67. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
68. (a) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; Wiley-VCH: Weinheim, 1996; pp 566-578.
69. (b) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
70. (a) Bader, R. R.; Baumeister, P.; Blaser, H.-U. Chimia 1996, 50, 99.
71. (b) Tsuji, J. Synthesis 1990, 739.
72. Rusanov, A. L.; Khotina, I. A.; Begretov, M. M. Usp. Khim. 1997, 66, 1162;
73. Russ. Chem. Rev. 1997, 66, 1053.
74. (a) Loch, J. A.; Albrecht, M.; Peris, E.; Mata, J.; Faller, J. W.; Crabtree, R. H. Organometallics 2002, 21, 700.
75. (b) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201.
76. McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741.
77. (a) Frey, G. D. Ph.D. Thesis, Technische Universität München, 2005.
78. (b) Schütz, J. Ph.D. Thesis, Technische Universität München, 2005.
79. (c) Frey, G. D.; Schütz, J.; Herdtweck, E.; Herrmann, W. A. Abstracts of Papers, 229th ACS National Meeting; San Diego, CA, March 13-17, 2005; INOR 226.
80. Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619.
81. Taube, R.; Steinborn, D.; Drews, H.; Chuong, P. N.; Stransky, N.; Langlotz, J. Z. Chem. 1988, 28, 381.
82. (a) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119;
83. Angew. Chem. Int. Ed. Engl. 1995, 34, 1021.
84. (b) Enders, D.; Breuer, K.; Teles, J. H.; Ebel, K. J. Prak. Chem. 1997, 339, 397.
85. (c) Enders, D.; Breuer, K.; Kallfass, U.; Balensiefer, T. Synthesis 2003, 8, 1292.
86. (a) Data Collection Software for Nonius κ-CCD devices; Delft, The Netherlands, 2001.
87. (b) Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307ff.
88. (c) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. SIR92. J. Appl. Crystallogr. 1994, 27, 435-436.
89. (d) International Tables for Crystallography, Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2.
90. (e) Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001.
91. (f) Sheldrick, G. M. SHELXL-97; Universität Göttingen: Göttingen, Germany, 1998.