1,3-Dialkyl- and 1,3-Diaryl-3,4,5,6-tetrahydropyrimidin-2-ylidene Rhodium(I) and Palladium,(II)Complexes: Synthesis, Structure, and Reactivity

Chemistry - A European Journal

Volumn 10, Issue 5, 2004, Pages 1256-1266

  Mayr, Monika ^a   Wurst, Klaus ^a   Ongania, Karl Hans ^a   Buchmeiser, Michael R ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

C C coupling; Carbene ligands; Homogeneous catalysis; Palladium; Rhodium

Indexed keywords

ADDITION REACTIONS; ALKALINITY; COMPLEXATION; CRYSTALLIZATION; MOLECULAR STRUCTURE; PALLADIUM COMPOUNDS; POSITIVE IONS; REACTION KINETICS; SILVER; SYNTHESIS (CHEMICAL);

TRANSMETALATION REACTIONS; TURNOVER NUMBERS (TON);

RHODIUM COMPOUNDS;

1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDINIUM BROMIDE; 1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDINIUM TETRAFLUOROBORATE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDINIUM BROMIDE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDINIUM TETRAFLUOROBORATE; 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE DERIVATIVE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BROMINE DERIVATIVE; BROMO N4 (1,5 CYCLOOCTADIENE)[1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; BROMO N4 (1,5 CYCLOOCTADIENE)[1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; CARBONYL DERIVATIVE; CHLORIDE; CHLORO N4 (1,5 CYCLOOCTADIENE)[1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; CHLORO N4 (1,5 CYCLOOCTADIENE)[1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; DICARBONYLCHLORO[1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; DICARBONYLCHLORO[1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]RHODIUM; HETEROCYCLIC COMPOUND; LIGAND; LITHIUM DERIVATIVE; LITHIUM TERT BUTOXIDE; PALLADIUM COMPLEX; PYRIMIDINE DERIVATIVE; RHODIUM COMPLEX; SILVER BIS[1,3 BIS(2 PROPYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]SILVER DIBROMIDE; SILVER BIS[1,3 BIS(2,4,6 TRIMETHYLPHENYL) 3,4,5,6 TETRAHYDROPYRIMIDIN 2 YLIDENE]SILVER DIBROMIDE; SILVER DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ALKALINITY; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CORRELATION ANALYSIS; CRYSTALLIZATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 1642410408     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305437     Document Type: Article

References (75)

1. K. Öfele, J. Organomet. Chem. 1968, 12, P42-P43.
2. H. W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int Ed. Engl. 1962, 1, 75-80.
3. H. W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int Ed. Engl. 1962, 1, 75-80.
4. H. W. Wanzlick, H. J. Schönherr, Angew. Chem. 1968, 80, 154-155; Angew. Chem. Int. Ed. Engl. 1968, 7, 141-142.
5. H. W. Wanzlick, H. J. Schönherr, Angew. Chem. 1968, 80, 154-155; Angew. Chem. Int. Ed. Engl. 1968, 7, 141-142.
6. A.J. Arduengo III, H.V. Rasika Dias, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 1992, 114, 5530-5534.
7. A.J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363.
8. R. W. Alder, P. R. Allen, S.J. Williams, Chem. Commun. 1995, 1267-1268.
9. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
10. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
11. T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 2000, 600, 12-22.
12. M. Regitz, Angew. Chem. 1996, 108, 791-794; Angew. Chem. Int. Ed. Engl. 1996, 35, 725-728.
13. M. Regitz, Angew. Chem. 1996, 108, 791-794; Angew. Chem. Int. Ed. Engl. 1996, 35, 725-728.
14. W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Chem. Eur. J. 1996, 2, 772-780.
15. J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674-2678.
16. J. Huang, H.-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5375-5380.
17. D. S. McGuinness, K. J. Cavell, B. W. Skelton, A. H. White, Organometallics 1999, 18, 1596-1605.
18. D. S. McGuinness, K. J. Cavell, Organometallics 2000, 19, 741-748.
19. C. W. Bielawski, R.H. Grubbs, Angew. Chem. 2000, 112, 3025-3028; Angew. Chem. Int. Ed. 2000, 39, 2903-2906.
20. C. W. Bielawski, R.H. Grubbs, Angew. Chem. 2000, 112, 3025-3028; Angew. Chem. Int. Ed. 2000, 39, 2903-2906.
21. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
22. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
23. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. 1998, 110, 2631-2633; Angew. Chem. Int. Ed. 1998, 37, 2490-2492.
24. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. 1998, 110, 2631-2633; Angew. Chem. Int. Ed. 1998, 37, 2490-2492.
25. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573-2576; Angew. Chem. Int. Ed. 1999, 38, 2416-2419.
26. T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573-2576; Angew. Chem. Int. Ed. 1999, 38, 2416-2419.
27. V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, J. Organomet. Chem. 2000, 595,186-190.
28. M. Tafipolsky, W. Scherer, K. Öfele, G. Artus, B. Pedersen, W. A. Herrmann, G. S. McGrady, J. Am. Chem. Soc. 2002, 124, 5865-5880.
29. T. Weskamp, F. J. Kohl, W. A. Herrmann, J. Organomet. Chem. 1999, 582, 362-365.
30. R. W. Alder, M. E. Blake, C. Bortolotti, S. Bufali, C. P. Butts, E. Linehan, J. M. Oliva, G. Orpen, M. J. Quayle, Chem. Commun. 1999, 241-242.
31. R. W. Alder, M. E. Blake, S. Bufali, C. P. Butts, A. G. Orpen, J. Schütz, S. J. Williams, J. Chem. Soc. Perkin Trans. 1 2001, 1586-1593.
32. K. Denk, P. Sirsch, W. A. Herrmann, J. Organomet. Chem. 2002, 649, 219-224.
33. C. Heinemann, T. Müller, Y. Apeloig, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 2023-2038.
34. A. H. Cowley, J. Organomet. Chem. 2001, 617-618, 105-109.
35. L. R. Orelli, M. B. Garcia, I. A. Perillo, Heterocycles 2000, 53, 2437-2450.
36. W. A. Herrmann, J. Fischer, K. Öfele, G. R. J. Artus, J. Organomet. Chem. 1997, 530, 259-262.
37. C. K. Lee, J. C. C. Chen, K. M. Lee, C. W. Liu, I. J. B. Lin, Chem. Mater. 1999, 11, 1237-1242.
38. H. M. J. Wang, C. Y. L. Chen, I. J. B. Lin, Organometallics 1999, 18, 1216-1223.
39. A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663-1667.
40. K. S. Coleman, H. T. Chamberlayne, S. Turberville, M. L. H. Green, A. R. Cowley, Dalton Trans. 2003, 2917-2922.
41. J. F. Bringley, M. Rajeswaran, EP-A, EP 1324119 Al, 2003 [Chem. Abstr. 139: 76296].
42. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7.
43. G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436.
44. J. G. de Vries, Can. J. Chem. 2001, 79, 1086-1092.
45. A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
46. A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
47. A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989-7000.
48. T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301-309.
49. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
50. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
51. W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1847.
52. W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1847.
53. W. A. Herrmann, V. P. W. Böhm, J. Organomet. Chem. 1999, 572, 141-145.
54. W. A. Herrmann, C. Broßmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357-1364.
55. A. Zapf, M. Beller, Chem. Eur. J. 2001, 7, 2908-2915.
56. W. A. Herrmann, C. P. Reisinger, K. Öfele, C. Broßmer, M. Beller, H. Fischer, J. Mol. Catal. 1996, 108, 51-56.
57. W. A. Herrmann, V. P. W. Böhm, C. W. K. Gstöttmayr, M. Grosche, C.-P. Reisinger, T. Weskamp, J. Organomet. Chem. 2001, 617-618, 616-628.
58. W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93-96.
59. J. Schwarz, V. P. W. Böhm, M. G. Gardiner, M. Grosche, W. A. Herrmann, W. Hieringer, G. Raudaschl-Sieber, Chem. Eur. J. 2000, 6, 1773-1780.
60. A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White, B. W. Skelton, J. Organomet. Chem. 2001, 617-618, 546-560.
61. A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10-11.
62. M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257-259.
63. A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem. 2001, 1131-1133.
64. A. H. M. de Vries, J. M. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285-3288.
65. Q. Yao, E.P. Kinney, Z. Yang, J. Org. Chem. 2003, 68, 7528-7531.
66. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321.
67. M. Mayr, M. R. Buchmeiser, Macromol. Rapid. Commun. 2004, 25, 231-236.
68. W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374.
69. W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374.
70. G. T. Crisp, M. G. Gebauer, Tetrahedron 1996, 52, 12465-12474.
71. M. R. Buchmeiser, K. Wurst, J. Am. Chem. Soc. 1999, 121, 11101-11107.
72. J. Silberg, T. Schareina, R. Kempe, K. Wurst, M. R. Buchmeiser, J. Organomet. Chem. 2000, 622, 6-18.
73. M. R. Buchmeiser, T. Schareina, R. Kempe, K. Wurst, J. Organomet. Chem. 2601, 634, 39-46.
74. Z. Otwinowski, W. Minor, Methods in Enzymology, Vol. 276, Academic Press, New York, 1997.
75. G. M. Sheldrick, Program package SHELXTL V.5.1, Bruker Analytical X-Rav Instruments Inc., Madison, 1997.