The carbene reactivity surface: A classification

Journal of Organic Chemistry

Volumn 73, Issue 4, 2008, Pages 1553-1558

  Mieusset, Jean Luc ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC ALKYL AMINO CARBENE; ELECTROPHILIC CARBENES; NUCLEOPHILIC CARBENES;

ACETONITRILE; CHEMICAL BONDS; CHEMICAL REACTIVITY; NUCLEOPHILES; SURFACE REACTIONS;

HYDROCARBONS;

ACETONITRILE; AMINOPHOSPHONIOCARBENE; BUTANE; CARBENE; CARBENOID; CYCLOPENTADIENYLIDENE; UNCLASSIFIED DRUG;

ARTICLE;

EID: 39349097867     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7026118     Document Type: Article

References (105)

1. (a) Brinker, U. H., Ed. Advances in Carbene Chemistry; Elsevier: New York, 2001; Vol. 3.
2. (b) Bertrand, G., Ed. Carbene Chemistry; Marcel Dekker: New York, 2002.
3. (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
4. (d) Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697.
5. (e) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
6. (f) Kirmse, W. Angew. Chem., Int. Ed. 2003, 42, 1088.
7. (g) Kirmse, W. Eur. J. Org. Chem. 2005, 237.
8. (h) Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348.
9. (a) Schoeller, W. W.; Brinker, U. H. Z. Naturforsch. 1980, 35b, 475.
10. (b) Schoeller, W. W. Tetrahedron Lett. 1980, 21, 1505.
11. (c) Schoeller, W. W.; Aktekin, N.; Friege, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 932.
12. (d) Moreno, M.; Lluch, J. M.; Oliva, A.; Bertran, J. J. Chem. Soc., Perkin Trans. 2 1986, 183.
13. (e) Soundararajan, N.; Platz, M. S.; Jackson, J. E.; Doyle, M. P.; Oon, S.-M.; Liu, M. T. H.; Anand, S. M. J. Am. Chem. Soc. 1988, 110, 7143.
14. (f) Fujimoto, H.; Ohwaki, S.; Endo, J.; Fukui, K. Gazz. Chim. Ital. 1990, 120, 229.
15. (g) Sigrist, H.; Muehlemann, M.; Dolder, M. J. Photochem. Photobiol. B 1990, 7, 277.
16. (h) Volovik, S. V.; Staninets, V. I.; Zefirov, N. S. Dokl. Akad. Nauk 1992, 324, 354.
17. (i) Mendez, F.; Garcia-Garibay, M. A. J. Org. Chem. 1999, 64, 7061.
18. (a) Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938.
19. (b) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.
20. (c) Mayr, H.; Ofial, A. R. Pure Appl. Chem. 2005, 77, 1807.
21. (d) Phan, T. B.; Breugst, M.; Mayr, H. Angew. Chem., Int. Ed. 2006, 45, 3869.
22. Terrier, F.; Lakhdar, S.; Boubaker, T.; Goumont, R. J. Org. Chem. 2005, 70, 6242.
23. (a) Moss, R. A. Acc. Chem. Res. 1980, 13, 58.
24. (b) Moss. R. A. Acc. Chem. Res. 1989, 22, 15.
25. Rondan, N. G.; Houk, K. N.; Moss. R. A. J. Am. Chem. Soc. 1980, 102, 1770.
26. (a) Parr, R. G.; Szentpály, L. v.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922.
27. (b) Chattaraj, P. K.; Sarkar, U.; Roy, D. R. Chem. Rev. 2006, 106, 2065.
28. Perez, P. J. Phys. Chem. A 2003, 107, 522.
29. Sander, W.; Kötting, C.; Hübert, R. J. Phys. Org. Chem. 2000, 13, 561.
30. (a) Bach, R. D.; Su, M.-D.; Aldabbagh, E.; Andrés, J. L.; Schlegel, H. B. J. Am. Chem. Soc. 1993, 115, 10237.
31. (b) Ramalingam, M.; Ramasami, K.; Venuvanalingam, P.; Sethuraman, V. THEOCHEM 2005, 755, 169.
32. Frisch, M. J. et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
35. Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 10211.
36. (a) Jaun, B.; Schwarz, J.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5741.
37. (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 252.
38. Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
39. Substituted cyclopentadienylidenes have already been ranked according to their selectivity: (a) Dürr, H. Top. Curr. Chem. 1973, 40, 103.
40. (b) Dürr, H. Top. Curr. Chem. 1975, 55, 87.
41. Sevin, F.; McKee, M. L.; Shevlin, P. B. J. Org. Chem. 2004, 69, 382.
42. (a) Zub, L. L.; Standard, J. M. THEOCHEM 1996, 368, 133.
43. (b) Tucker, J. M.; Standard, J. M. THEOCHEM 1998, 431, 193.
44. (c) Gonzalez, C.; Restrepo-Cossio, A.; Marquez, M.; Wiberg, K. B. J. Am. Chem. Soc. 1996, 118, 5408.
45. (d) Yates, B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250.
46. (e) Moreno, M.; Lluch, J. M; Oliva, A.; Bertran, J. Can. J. Chem. 1987, 65, 2774.
47. (f) Dobado, J. A.; Martinez-Garcia, H.; Molina, J. M.; Sundberg, M. R. J. Am. Chem. Soc. 2000, 122, 1144.
48. (g) Oku, A.; Sawada, Y.; Schroeder, M.; Higashikubo, I.; Yoshida, T.; Ohki, S. J. Org. Chem. 2004, 69, 1331.
49. (a) McKellar, A. R. W.; Bunker, P. R.; Sears, T. J.; Evenson, K. M.; Saykally, R. J.; Langhoff, S. R. J. Chem. Phys. 1983, 79, 5251.
50. (b) Zuev, P. S.; Sheridan, R. S. J. Am. Chem. Soc. 2001, 123, 12434.
51. (c) Kassaee, M. Z.; Arshadi, S.; Acedy, M.; Vessally, E. J. Organomet. Chem. 2005, 690, 3427.
52. (d) Scott, A. P.; Platz, M. S.; Radom, L. J. Am. Chem. Soc. 2001, 123, 6069.
53. Takahashi, Y.; Nicolaides, A.; Tomioka, H. J. Synth. Org. Chem. Jpn. 2001, 59, 1070.
54. Chateauneuf, J. E.; Johnson, R. P.; Kirchhoff, M. M. J. Am. Chem. Soc. 1990, 112, 3217.
55. Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 8434.
56. (a) Dehmlow, E. V. In Houben-Weyl (Methoden der Organischen Chemie); Regitz, M. Ed.; Thieme: Stuttgart, Germany, 1989; Vol. E 19b, pp 1521-1589.
57. (b) Masaki, Y.; Arasaki, H.; Shiro, M. Chem. Lett. 2000, 29, 1180.
58. (c) Masaki, Y.; Arasaki, H.; Iwata, M. Chem. Lett. 2003, 32, 4.
59. (d) Arasaki, H.; Iwata, M.; Makida, M.; Masaki, Y. Chem. Pharm. Bull. 2004, 52, 848.
60. (e) Zlotskii, S. S.; Bazunova, G. G.; Mikhailova, N. N. Bashk. Khim. Zh. 2005, 12, 21.
61. (f) Masaki, Y. Gifu Yakka Daigaku Kiyo 2005, 54, 29.
62. (a) Lin, Q.-J.; Feng, D.-C.; Qi, C.-S. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1922.
63. (b) Feng, D.-C.; Lin, Q.-J.; Ma, W.-Y.; Wang, H.-J. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1708.
64. (c) Lin, Q.-J.; Feng, D.-C.; Ma, W.-Y. Gaodeng Xuexiao Huaxue Xuebao 2000, 21, 1427.
65. (d) Lin, Q.-J.; Feng, D.-C.; Qi, C.-S. Jiegou Huaxue 2000, 19, 224.
66. Ramalingam, M.; Ramasami, K.; Venuvanalingam, P. Chem. Phys. Lett. 2006, 430, 414.
67. Mieusset, J.-L.; Brinker, U. H. J. Am. Chem. Soc. 2006, 128, 15843.
68. (a) Merceron-Saffon, N.; Baceiredo, A.; Gornitzka, H.; Bertrand, G. Science 2003, 301, 1223.
69. (b) Conejero, S.; Canac, Y.; Tham, F. S.; Bertrand, G. Angew. Chem., Int. Ed. 2004, 43, 4089.
70. (c) Vignolle, J.; Donnadieu, B.; Bourissou, D.; Bertrand, G. Tetrahedron Lett. 2007, 48, 685.
71. Korotkikh, N. I.; Rayenko, G. F.; Shvaika, O. P.; Pekhtereva, T. M.; Cowley, A. H.; Jones, J. N.; Macdonald, C. L. B. J. Org. Chem. 2003, 68, 5762.
72. Arduengo, A. J., III; Calabrese, J. C.; Davidson, F.; Rasika Dias, H. V.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J.; Tamm, M.; Schmutzler, R. Helv. Chim. Acta 1999, 82, 2348.
73. See also: (a) Solé, S.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Science 2001, 292, 1901.
74. (b) Cunico, R. F. Tetrahedron Lett. 2001, 42, 2931.
75. (c) Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem. Eur. J. 2004, 10, 4073.
76. (d) Lloyd-Jones, G. C.; Alder, R. W.; Owen-Smith, G. J. J. Chem. Eur. J. 2006, 12, 5361.
77. However, it has to be emphasized that the concerted biphilic pathway is widely accepted as the dominating pathway for C-H insertion of usual carbenes. Especially, the stepwise mechanism described for electrophilic carbenes in ref 30 should only be considered if the negative and the positive charge can be efficiently stabilized.
78. (a) Öfele, K. Angew. Chem., Int. Ed. Engl. 1968, 7, 950.
79. (b) Herrmann, W. A.: Öfele, K.; Schneider, S. K.; Herdtweck, E.; Hoffmann, S. D. Angew. Chem., Int. Ed. 2006, 45, 3859.
80. (c) Wass, D. F.; Haddow, M. F.; Hey, T. W.; Orpen, A. G.; Russell, C. A.; Wingad, R. L.; Green, M. Chem. Commun. 2007, 26, 2704.
81. (d) Wass, D. F.; Hey, T. W.; Rodriguez-Castro, J.; Russell, C. A.; Shishkov, I. V.; Wingad, R. L.; Green, M. Organometallics 2007, 26, 4702.
82. (a) Lavallo, V.; Canac, Y.; DeHope, A.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 7236.
83. (b) Jazzar, R.; Dewhurst, R. D.; Bourg, J.-B.; Donnadieu, B.; Canac, Y.; Bertrand, G. Angew. Chem., Int. Ed. 2007, 46, 2899.
84. (c) Anderson, D. R.; Lavallo, V.; O'Leary, D. J.; Bertrand, G.; Grubbs, R. H. Angew. Chem., Int. Ed. 2007, 46, 7262.
85. (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457.
86. (b) Dürr, H. In Methoden der Organischen Chemie, Houben Weyl; Regitz, M., Ed.; Thieme Verlag: Stuttgart, Germany 1989; Vol. E19b, p 778.
87. Reisenauer, H. P.; Maier, G.; Riemann, A.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1984, 23, 641.
88. (a) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2005, 70, 10572.
89. (b) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2006, 71, 6975.
90. (c) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 263.
91. (a) Kirmse, W.; Meinen, T. J. Chem. Soc., Chem. Commun. 1994, 1065.
92. (b) Alberti, J.; Siegfried, R.; Kirmse, W. Liebigs Ann. Chem. 1974, 1605.
93. Tomioka, H.; Hirai, K.; Tabayashi, K.; Murata, S.; Izawa, Y.; Inagaki, S.; Okajima, T. J. Am. Chem. Soc. 1990, 112, 7692.
94. (a) Jones, W. M.; Brinker, U. H. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. 1, p 123.
95. (b) Misslitz, U.; de Meijere, A. In Methoden der Organischen Chemie, Houben Weyl; Regitz, M., Ed.; Thieme Verlag: Stuttgart, Germany 1989; Vol. E19b, p 664.
96. (c) Baird, M. S. Chem. Rev. 2003, 103, 1271.
97. (a) Hoffmann, R.; Zeiss, G. D.; Van Dine, G. W. J. Am. Chem. Soc. 1968, 90, 1485.
98. (b) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287.
99. (c) Bonneau, R.; Liu, M. T. H. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, NY, 1998; Vol. 2, p 1.
100. (d) Pezacki, J. P.; Couture, P.; Dunn, J. A.; Warkentin, J.; Wood, P. D.; Lusztyk, J.; Ford, F.; Platz, M. S. J. Org. Chem. 1999, 64, 4456.
101. (e) Creary, X.; Butchko, M. A. J. Am. Chem. Soc. 2001, 123, 1569.
102. (f) Albu, T. V.; Lynch, B. J.; Truhlar, D. G.; Goren, A. C.; Hrovat, D. A.; Borden, W. T.; Moss, R. A. J. Phys. Chem. A 2002, 106, 5323.
103. (g) Hill, B. T.; Zhu, Z.; Boeder, A.; Hadad, C. M.; Platz, M. S. J. Phys. Chem. A 2002, 106, 4970.
104. (h) Kraka, E.; Cremer, D. J. Phys. Org. Chem. 2002, 15, 431.
105. (i) Dkhar, P. G. S.; Lyngdoh, R. H. D. Indian J. Chem. 2005, 44B, 2138.