Stable P-heterocyclic carbenes: Scope and limitations

Chemistry - An Asian Journal

Volumn 2, Issue 1, 2007, Pages 178-187

  Masuda, Jason D ^a   Martin, David ^a,b   Lyon Saunier, Celine ^b   Baceiredo, Antoine ^b   Gornitzka, Heinz ^b   Donnadieu, Bruno ^a   Bertrand, Guy ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UMR 5069) 118 route de Narbonne   (France)

Author keywords

Carbenes; Heterocycles; Ligands; Phosphorus; Transition metals

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROCARBON; METHANE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; METHANE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHINES;

EID: 33846321849     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600300     Document Type: Article

References (108)

1. For general reviews on stable carbenes: a) F. E. Hahn, Angew. Chem. 2006, 118, 1374;
2. Angew. Chem. Int. Ed. 2006, 45, 1348;
3. b) W. Kirmse, Angew. Chem. 2004, 116, 1799;
4. Angew. Chem. Int. Ed. 2004, 43, 1767;
5. c) R. W. Alder, M. E. Blake, M. E. Chaker, J. N. Harvey, F. Paolini, J. Schütz, Angew. Chem. 2004, 116, 6020;
6. Angew. Chem. Int. Ed. 2004, 43, 5896;
7. d) Y. Canac, M. Soleilhavoup, S. Conejero, G. Bertrand, J. Organomet. Chem. 2004, 689, 3857;
8. e) D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39.
9. For reviews on stable carbenes as ligands for transition metal catalysts; a) N. M. Scott, S. P. Nolan, Eur. J. Inorg. Chem. 2005, 1815;
10. b) N. Kuhn, A. Al-Sheikh, Coord. Chem. Rev. 2005, 249, 829;
11. c) E. Peris, R. H. Crabtree, Coord. Chem. Rev. 2004, 248, 2239;
12. d) C. M. Crudden, D. P. Allen, Coord. Chem. Rev. 2004, 248, 2247;
13. e) V. César, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 2004, 33, 619;
14. f) D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534;
15. g) M. C. Perry, K. Burgess, Tetrahedron: Asymmetry 2003, 14, 951;
16. h) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
17. Angew. Chem. Int. Ed. 2002, 41, 1290;
18. i) L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181;
19. j) D. Enders, H. Gielen, J. Organomet. Chem. 2001, 617-618, 70.
20. For examples, see: a) E. Despagnet, K. Miqueu, H. Gornitzka, P. W. Dyer, D. Bourissou, G. Bertrand, J. Am. Chem. Soc. 2002, 124, 11 834;
21. b) X. Cattoën, H. Gornitzka, D. Bourissou, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 1342;
22. c) V. Lavallo, J. Mafhouz, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 8670;
23. d) K. Denk, P. Sirsch, W. A. Herrmann, J. Organomet. Chem. 2002, 649, 219;
24. e) N. Merceron-Saffon, H. Gornitzka, A. Baceiredo, G. Bertrand, J. Organomet. Chem. 2004, 689, 1431.
25. a) W. A. Herrmann, K. Ofele, D. von Preysing, E. Herdtweck, J. Organomet. Chem. 2003, 684, 235;
26. b) W. W. Schoeller, D. Eisner, S. Grigoleit, A. R. Rozhenko, A. Alijah, J. Am. Chem. Soc. 2000, 122, 10 115.
27. a) V. Lavallo, Y. Canac, C. Prasang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851;
28. Angew. Chem. Int. Ed. 2005, 44, 5705;
29. b) V. Lavallo, Y. Canac, A. Dehope, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 7402;
30. Angew. Chem. Int. Ed. 2005, 44, 7236.
31. a) V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2006, 312, 722;
32. b) V. Lavallo, Y. Ishida, B. Donnadieu, G. Bertrand, Angew. Chem. 2006, 118, 6804;
33. Angew. Chem. Int. Ed. 2006, 45, 6652.
34. J. Kapp, C. Schade, A. M. El-Nahasa, P. von R. Schleyer, Angew. Chem. 1996, 108, 2373;
35. Angew. Chem. Int. Ed. Engl. 1996, 35, 2236.
36. L. Nyulászi, Tetrahedron 2000, 56, 79.
37. For calculations on PHCs, see: a) A. Fekete, L. Nyulászi, J. Organomet. Chem. 2002, 643-644, 278;
38. b) W. W. Schoeller, D. Eisner, Inorg. Chem. 2004, 43, 2585;
39. c) H. Jacobsen, J. Organomet. Chem. 2005, 690, 6068.
40. A titanocene and a zirconocene complex of a PHC have already been spectroscopically characterized: T. Cantat, N. Mézailles, N. Maigrot, L. Ricard, P. Le Floch, Chem. Commun. 2004, 1274.
41. A trimethylalane adduct of a cyclic anion with a diphosphinocarbene unit has been isolated: E. Niecke, A. Fuchs, M. Nieger, O. Schmidt, W. W. Schoeller, Angew. Chem. 1999, 111, 3216;
42. Angew. Chem. Int. Ed. 1999, 38, 3031.
43. Metalladiphosphinocarbenes are known as transient species: J. Ruiz, M. E. G. Mosquera, G. García, E. Patrón, V. Riera, S. García-Granda, F. Van der Maelen, Angew. Chem. 2003, 115, 4915;
44. Angew. Chem. Int. Ed. 2003, 42, 4767.
45. 2C] complexes have been isolated: N. D. Jones, G. Lin, R. A. Gossage, R. McDonald, R. G. Cavell, Organometallics 2003, 22, 2832.
46. A preliminary communication on this work: D. Martin, A. Baceiredo, H. Gornitzka, W. W. Schoeller, G. Bertrand, Angew. Chem. 2005, 117, 1728;
47. Angew. Chem. Int. Ed. 2005, 44, 1700.
48. + are unstable towards rearrangement: a) T. Kato, H. Gornitzka, A. Baceiredo, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2002, 124, 2506;
49. b) T. Kato, H. Gornitzka, A. Baceiredo, W. W. Schoeller, G. Bertrand, Science 2000, 289, 754.
50. 3) derivatives are known: a) M. Sebastian, O. Schmidt, A. Fuchs, M. Nieger, D. Szieberth, L. Nyulaszi, E. Niecke, Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 779;
51. b) A. Fuchs, M. Nieger, E. Niecke, L. Nyulaszi, O. Schmidt, W. Schoeller, M. Sebastian, Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 1605;
52. c) M. Sebastian, A. Hoskin, M. Nieger, N. Nyulaszi, E. Niecke, Angew. Chem. 2005, 117, 1429;
53. Angew. Chem. Int. Ed. 2005, 44, 1405.
54. a) H. H. Karsch, H. U. Reisacher, G. Muller, Angew. Chem. 1986, 98, 467;
55. Angew. Chem. Int. Ed. Engl. 1986, 25, 454;
56. b) H. H. Karsch, H. Reisacher, T. Ruprich in Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 3 (Ed.: W. A. Hermann), Thieme Verlag, Stuttgart, 1996, pp. 140.
57. a) A. H. Cowley, R. A. Kemp. Chem. Rev. 1985, 85, 367;
58. b) A. H. Cowley, ACS Symp. Ser. 2006, 917, 2;
59. c) N. Burford, P. J. Ragogna, ACS Symp. Ser. 2006, 917, 280.
60. H. H. Karsch, F. H. Köhler, H. Reisacher, Tetrahedron Lett. 1984, 25, 3687.
61. A. A. Prishchenko, Z. S. Novikova, J. F. Lutsenko, Z. Obshch. Khim. 1980, 50, 689.
62. a) A. Stasch, S. Singh, H. W. Roesky, M. Noltemeyer, H. G. Schmidt, Eur. J. Inorg. Chem. 2004, 4052;
63. b) A. Beste, O. Krämer, A. Gerhard, G. Frenking, Eur. J. Inorg. Chem. 1999, 2037,
64. c) A. H. Cowley, F. P. Gabbaï, C. J. Carrano, L. M. Mokry, M. R. Bond, G. Bertrand, Angew. Chem. 1994, 106, 584;
65. Angew. Chem. Int. Ed. Engl. 1994, 33, 578
66. a) A. Igau, A. Baceiredo, H. Grützmacher, H. Pritzkow, G. Bertrand, J. Am. Chem. Soc. 1989, 111, 6853;
67. b) O. Guerret, G. Bertrand, Acc. Chem. Res. 1997, 30, 486;
68. c) H. Grützmacher, H. Pritzkow, Angew. Chem. 1991, 103, 721;
69. Angew. Chem. Int. Ed. Engl. 1991, 30, 709;
70. d) G. Frenking, S. Fau, C. M. Marchand, H. Grützmacher. J. Am. Chem. Soc. 1997, 119, 6648;
71. e) H. Grützmacher, C. M. Marchand. Coord. Chem. Rev. 1997, 163, 287.
72. a) R. Appel, P. Fölling, B. Josten, M. Siray, V. Winkhaus, F. Knock, Angew. Chem. 1984, 96, 621;
73. Angew. Chem. Int. Ed. Engl. 1984, 23, 619;
74. b) H. H. Karsch, H. U. Reisacher, G. Muller, Angew. Chem. 1984, 96, 619;
75. Angew. Chem. Int. Ed. Engl. 1984, 23, 618;
76. c) H. H. Karsch, F. H. Köhler, H. U. Reisacher, Tetrahedron Lett. 1984, 25, 3687;
77. d) M. Yoshifuji, K. Toyota, N. Inamoto, J. Chem. Soc. Chem. Commun. 1984, 689;
78. e) H. H. Karsch, A. Appell, H. U. Reisacher, G. Müller, Phosphorus Sulfur Relat. Elem. 1987, 30, 417;
79. f) M. Yoshifuji, S. Sasaki, N. Inamoto, Tetrahedron Lett. 1989, 30, 839;
80. g) M. Gouygou, M. Koenig, J. Escudié, C. Couret, Heteroat. Chem. 1991, 2, 221;
81. h) M. Yoshifuji, S. Sasaki, T. Nütsu, N. Inamoto, Tetrahedron Lett. 1989, 30, 187;
82. i) M. Yoshifuji, S. Sasaki, N. Inamoto, J. Chem. Soc. Chem. Commun. 1989, 1732.
83. D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem. 1995, 107, 1119;
84. Angew. Chem. Int. Ed. Engl. 1995, 34, 1021.
85. M. K. Denk, J. M. Rodezno, S. Gupta, A. J. Lough, J. Organomet. Chem. 2001, 617, 242.
86. For examples, see: a) R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719;
87. b) D. Enders, O. Niemeier, T. Balensiefer, Angew. Chem. 2006, 118, 1491;
88. Angew. Chem. Int. Ed. 2006, 45, 1463;
89. c) H. Takikawa, Y. Hachisu, J. W. Bode, K. Suzuki, Angew. Chem. 2006, 118, 3572;
90. Angew. Chem. Int. Ed. 2006, 45, 3492;
91. d) M. S. Kerr, J. R. de Alaniz, T. Rovis, J. Org. Chem. 2005, 70, 5725;
92. e) C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331;
93. Angew. Chem. Int. Ed. 2004, 43, 6205;
94. f) D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534;
95. g) J. Pesch, K. Harms, T. Bach, Eur. J. Org. Chem. 2004, 9, 2025.
96. a) A. Igau, H. Grützmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463;
97. b) A. Igau, A. Baceiredo, G. Trinquier, G. Bertrand, Angew. Chem. 1989, 101, 617;
98. Angew. Chem. Int. Ed. Engl. 1989, 28, 621;
99. c) T. Kato, H. Gornitzka, A. Baceiredo, A. Savin, G. Bertrand, J. Am. Chem. Soc. 2000, 122, 998.
100. a) O. Illa, H. Gornitzka, V. Branchadell, A. Baceiredo, G. Bertrand, R. M. Ortuno, Eur. J. Org. Chem. 2003, 3147;
101. b) O. Illa, H. Gornitzka, A. Baceiredo, G. Bertrand, V. Branchadell, R. M. Ortuno, J. Org. Chem. 2003, 68, 7707.
102. M. Mayr, K. Wurst, K. H. Ongania, M. Buchmeiser, Chem. Eur. J. 2004, 10, 1256.
103. a) R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211;
104. Angew. Chem. Int. Ed. Engl. 1996, 35, 1121;
105. b) K. Denk, P. Sirsch, W. A. Herrmann, J. Organomet. Chem. 2002, 649, 219.
106. For computational considerations on new metathesis catalysts based on PHCs, see: a) W. W. Schoeller, D. Schroeder, A. B. Rozhenko, J. Organomet. Chem. 2005, 690, 6079;
107. b) H. Jacobsen, Dalton Trans. 2006, 18, 2214;
108. c) G. Occhipinti, H. R. Bjorsvik, J. Am. Chem. Soc. 2006, 128, 6952.