Metalloxy Fischer carbene complexes: An efficient strategy to modulate their reactivity

Tetrahedron

Volumn 56, Issue 27, 2000, Pages 4597-4628

  Barluenga, José ^a   Fañanás, Francisco J ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; CARBENE; METAL; TITANIUM; ZIRCONIUM;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; PRIORITY JOURNAL;

EID: 0343932676     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00237-4     Document Type: Review

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135. For details of benzannulation reaction mechanism see: (a) Hofmann, P.; Hämmerle, M.; Unfried, G. New. J. Chem. 1991, 15, 769. (b) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Pérez-Carreño, E. J. Am. Chem. Soc. 1994, 116, 11191. (c) Gleichmann, M. M.; Dötz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551. (d) Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298. (e) Torrent, M.; Durán, M.; Solá, M. J. Am. Chem. Soc. 1999, 121, 1308. (f) Waters, M. L.; Bos, M. E.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 6403. (g) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragaño, M. A. J. Am. Chem. Soc., 2000, 122, 1314.
136. For details of benzannulation reaction mechanism see: (a) Hofmann, P.; Hämmerle, M.; Unfried, G. New. J. Chem. 1991, 15, 769. (b) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Pérez-Carreño, E. J. Am. Chem. Soc. 1994, 116, 11191. (c) Gleichmann, M. M.; Dötz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551. (d) Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298. (e) Torrent, M.; Durán, M.; Solá, M. J. Am. Chem. Soc. 1999, 121, 1308. (f) Waters, M. L.; Bos, M. E.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 6403. (g) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragaño, M. A. J. Am. Chem. Soc., 2000, 122, 1314.
137. For details of benzannulation reaction mechanism see: (a) Hofmann, P.; Hämmerle, M.; Unfried, G. New. J. Chem. 1991, 15, 769. (b) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Pérez-Carreño, E. J. Am. Chem. Soc. 1994, 116, 11191. (c) Gleichmann, M. M.; Dötz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551. (d) Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298. (e) Torrent, M.; Durán, M.; Solá, M. J. Am. Chem. Soc. 1999, 121, 1308. (f) Waters, M. L.; Bos, M. E.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 6403. (g) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragaño, M. A. J. Am. Chem. Soc., 2000, 122, 1314.
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149. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
150. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
151. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
152. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
153. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
154. For other examples of C-H insertion reaction in nonheteroatom-stabilized Fischer carbene complexes, see: (a) Fischer, H.; Schmid, J.; Maerkl, R. J. Chem. Soc., Chem. Commun. 1985, 572. (b) Fischer, H.; Schmid, J. J. Mol. Catal. 1988, 46, 277. (c) Zhao, S. K.; Knors, C.; Helquist, P. J. Am. Chem. Soc. 1989, 111, 8527. (d) Zhao, S. K.; Helquist, P. J. Org. Chem. 1990, 55, 5820. (e) Zhao, S.; Mehta, G.; Helquist, P. Tetrahedron Lett. 1991, 32, 5753. (f) Wang, S. L. B.; Su, J.; Wulff, W. D.; Hoogsteen, K. J. Am. Chem. Soc. 1992, 114, 10665. (g) Fischer, H.; Jungklaus, H. J. Organomet. Chem. 1999, 572, 105.
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170. For representative examples of intermolecular addition of acyl radicals to electron-deficient alkenes, see: (a) Schefford, R.; Orlinski, R. J. Am. Chem. Soc. 1983, 105, 7200. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (c) Ryu, I.; Kusano, K.; Yamazaki, H.; Sonoda, N. J. Org. Chem. 1991, 56, 5003. (d) Ryu, I.; Yamazaki, H.; Kusano, K.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558. (e) Giese, B.; Thoma, G. Helv. Chim. Acta 1991, 74, 1143. (f) Ryu, I.; Hagesawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda, N. Synlett 1993, 143. (g) Punniyamurthy, T.; Bhatia, B.; Iqbal, J. J. Org. Chem. 1994, 59, 850.
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