Catalytic transmetalation of alkoxychromium(0) carbenes to late transition metals: Self-dimerization and cyclopropanation reactions

Organometallics

Volumn 23, Issue 21, 2004, Pages 5021-5029

  Del Amo, Juan C ^a   Mancheño, María J ^a   Gómez Gallego, Mar ^a   Sierra, Miguel A ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DIMERIZATION; MIXTURES; REDUCTION; STOICHIOMETRY; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CATALYTIC TRANSMETALATION; ORGANIC SYNTHESIS; STOICHIOMETRIC REACTIONS;

ORGANOMETALLICS;

EID: 6344294323     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049455d     Document Type: Article

References (82)

1. Reviews: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1983.
2. (b) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.
3. (c) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 1065.
4. (d) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143,
5. (e) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503.
6. (f) Grotjahn, D. B.; Dötz, K. H. Synlett. 1991, 381.
7. (g) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 470.
8. (h) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 549.
9. (i) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
10. (j) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
11. (k) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163.
12. (l) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A. Curr. Org. Chem. 1998, 2, 561,
13. (m) Sierra, M. A. Chem. Rev. 2000, 100, 3591,
14. (n) de Metjere, A.; Schirmer, H.; Duetsoh, M. Angew. Chem., Int. Ed. 2000, 39, 3964.
15. (o) Barluenga, J.; Flórez, J.; Fañanás, F. J. J. Organomet. Chem. 2001, 624, 5.
16. For an overview of the stoichiometric transmetalation from group 6 metal-carbene complexes to different transition metals, see: Liu, S.-T-; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315.
17. Sierra, M. A.; Mancheño, M. J.; Sáez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
18. (a) Sierra, M. A.; del Amo, J. C.; Mancheño, M. J.; Gómez-Gallego, M. J. Am. Chem. Soc. 2001, 123, 851.
19. (b) Sierra, M. A.; del Amo, J. C.; Mancheño, M. J.; Gómez-Gallego, M.; Torres, M. R. Chem. Commun. 2002, 1842.
20. (c) Sakurai, H.; Tanabe, K.; Narasaka, K. Chem. Lett. 1999, 309.
21. (d) Sakurai, H.; Tanabe, K.; Narasaka, K. Chem. Lett. 2000, 168.
22. (e) Yamane, M.; Ishibashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 2000, 174.
23. (a) Aumann, R.; Göttker-Sohnetmann, I.; Fröhlich, R.; Meyer, O. Eur. J. Org. Chem. 1999, 2545.
24. (b) Aumann, R.; Göttker-Sohnetmann, I.; Fröhlich, R.; Meyer, O. Eur. J. Org. Chem. 1999, 3209.
25. (c) Göttker-Schnetmann, I.; Aumann, R. Organometallics 2001, 20, 346.
26. (d) Göttker-Schnetmann, I.; Aumann, R.; Bergander, K. Organometallics 2001, 20, 3574.
27. (e) Barluenga, J.; Vicente, R.; López, L. A.; Rubio, E.; Tomás, M.; Álvarez-Rúa, C. J. Am. Chem. Soc. 2004, 126, 470.
28. Barluenga, J.; Barrio, P.; López, L. A.; Tomás, M.; Garcíe-Granda, S.; Álvarez-Rúa, C. Angew. Chem., Int. Ed. 2003, 42, 3008.
29. Barluenga, J.; López, L. A.; Löber, O.; Tomás, M.; García-Granda, S.; Álvarez-Rúa, C.; Borge, J. Angew. Chem., Int. Ed. 2001, 40, 3392.
30. Albéniz, C.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2363.
31. Prepared following the literature methods, see: (a) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819. (b) Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2003, 68, 1177. (c) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
32. Prepared following the literature methods, see: (a) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819. (b) Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2003, 68, 1177. (c) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
33. Prepared following the literature methods, see: (a) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819. (b) Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2003, 68, 1177. (c) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
34. (a) Kubiak, C. P. In Comprenheaive Organometallic Chemistry II; Abel, E. W., Stone, P. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 9, p 1. From an overview on recent Ni catalysts and their application in organic chemistry, see: (b) New Developments in Organonickel Chemistry. Tetrahedron Symposium-in-Print, no. 69: Lipshutz, B. H., Luh, T. Y., Eds. Tetrahedron 1998, 54, 1021.
35. (a) Kubiak, C. P. In Comprenheaive Organometallic Chemistry II; Abel, E. W., Stone, P. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 9, p 1. From an overview on recent Ni catalysts and their application in organic chemistry, see: (b) New Developments in Organonickel Chemistry. Tetrahedron Symposium-in-Print, no. 69: Lipshutz, B. H., Luh, T. Y., Eds. Tetrahedron 1998, 54, 1021.
36. 3. For the use of these conditions in catalytic reactions, see: (a) Zembayashi, M.; Tamao, K.; Yoshida, J.-I.; Kumada, M. Tetrahedron Lett. 1977, 4089. For the use of these conditions in stoichiometric reactions, see: (b) Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 3375.
37. 3. For the use of these conditions in catalytic reactions, see: (a) Zembayashi, M.; Tamao, K.; Yoshida, J.-I.; Kumada, M. Tetrahedron Lett. 1977, 4089. For the use of these conditions in stoichiometric reactions, see: (b) Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 3375.
38. See, among others: (a) Eisch, J. J. Pure Appl. Chem. 1984, 56, 35. (b) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319.
39. See, among others: (a) Eisch, J. J. Pure Appl. Chem. 1984, 56, 35. (b) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319.
40. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotrnsition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
41. (b) Lantus, M.; Fajnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
42. (c) Briout, H.; Carpentier, J. F.; Mortreux, A. J. Mol. Catal. A Chem. 1998, 136, 243.
43. (d) van der Boom, M. E.; Lion, S.-Y.; Ben-David, Y.; Shinon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 6531.
44. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
45. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
46. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
47. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
48. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
49. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
50. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
51. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
52. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
53. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
54. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
55. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
56. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
57. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
58. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
59. For reviews about cyclopropanation reactions using Fischer carbene complexes see: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Able, E. W., Stone, F. G. A., Wilkinson, G.. Eds.; Pergamon: Oxford, 1995; Vol. 12, p 387. (b) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. Selected examples: (c) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1970, 103, 1273. (d) Dötz, K. H.; Fischer, E. O. Chem. Ber. 1972, 105, 1356. (e) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966. (f) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Yeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574. (g) Casey, C. P.; Vollendorf, N. W.; Haller, K. J. J. Am. Chem. Soc. 1984, 106, 3754. (h) Casey, C. P.; Shusterman, A. J. Organometallics 1985, 4, 736. (i) Casey, C. P.; Hornung, N. L.; Kosar, W. P. J. Am. Chem. Soc. 1987, 109, 4908. (j) Södeberg, B. C.; Hegedus, L. S. Organometallics 1990, 9, 3113. (k) Barluenga, J.; Montserrat, J. M.; Flórez, J. J. Chem. Soc., Chem. Commun. 1993, 1068. (l) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73. Ullman, A.; Gruner, M.; Reissig, H.-U. Chem. Eur. J. 1999, 5, 187. (n) Barluenga, J.; Fernández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591. (o) Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719.
60. Examples of cyclopropanation reactions using Fischer carbene complexes under mild conditions: Photochemical: (a) Sierra, M. A.; Del Amo, J. C.; Mancheño, M. J.; Gómez-Gallego, M. Tetrahedron Lett. 2001, 42, 5435.
61. Thermal: (b) Wulff, W. D.; Yang, D. C.; Murray, C. K. J. Am. Chem. Soc. 1988, 110, 2653.
62. Leadbeater, N. E. J. Org. Chem. 2001, 66, 7539.
63. (a) Simmons, H. B.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323.
64. (b) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256.
65. (c) Rawson, R. J.; Harrison, I. T. J. Org. Chem. 1970, 36, 2057. For an extensive review, see ref 15a.
66. The formation of 4-oxo eaters has been reported in diverse thermal reactions of alkoxy, acyloxy, and amino carbene ohromium(0) complexes and electron-deficient olefins. See, among others: (a) Wienand, A.; Reissig, H.-U. Organometallics 1990, 9, 3133. (b) Sierra, M. A.; Soderbeg, B. C.; Lander, P. A.; Hegedus, L. S. Organometallics 1993, 12, 3769. (c) Soderberg, B. C.; York, D. C.; Harriston, E. A.; Caprara, K. J.; Flurry, A. H. Organometallics 1995, 14, 3712.
67. The formation of 4-oxo eaters has been reported in diverse thermal reactions of alkoxy, acyloxy, and amino carbene ohromium(0) complexes and electron-deficient olefins. See, among others: (a) Wienand, A.; Reissig, H.-U. Organometallics 1990, 9, 3133. (b) Sierra, M. A.; Soderbeg, B. C.; Lander, P. A.; Hegedus, L. S. Organometallics 1993, 12, 3769. (c) Soderberg, B. C.; York, D. C.; Harriston, E. A.; Caprara, K. J.; Flurry, A. H. Organometallics 1995, 14, 3712.
68. The formation of 4-oxo eaters has been reported in diverse thermal reactions of alkoxy, acyloxy, and amino carbene ohromium(0) complexes and electron-deficient olefins. See, among others: (a) Wienand, A.; Reissig, H.-U. Organometallics 1990, 9, 3133. (b) Sierra, M. A.; Soderbeg, B. C.; Lander, P. A.; Hegedus, L. S. Organometallics 1993, 12, 3769. (c) Soderberg, B. C.; York, D. C.; Harriston, E. A.; Caprara, K. J.; Flurry, A. H. Organometallics 1995, 14, 3712.
69. Heptacoordinated Cr-carbene complexes have been previously reported: (a) Stumpf, R.; Jaeger, M.; Fischer, H. Organometallics 2000, 19, 4040.
70. (b) Jaeger, M.; Stumpf, T.; Carsten, T.; Fischer, H. Chem. Commun. 2000, 931, and the pertinent references therein.
71. Fischer, E. O.; Aumann, R. Chem. Ber. 1968, 101, 963.
72. Fischer, E. O.; Maasböl, A. J. Organomet. Chem. 1968, 12, P15.
73. Hafner, A.; Hegedus, L. S.; de Weck, G.; Hawkins, B.; Dötz, K. H. J. Am. Chem. Soc. 1988, 110, 8413.
74. Aumann, R.; Heinen, H. Chem. Ber. 1987, 120, 537.
75. (a) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1988, 108, 5229.
76. (b) Duetsch, M.; Stein, F.; Lackman, R.; Pohl, E.; Herbst-Irmer, R.; de Meijere, A. Chem. Ber. 1992, 125, 2051.
77. (c) Aumann, R.; Hinterding, P. Chem. Ber. 1993, 126, 421.
78. 2-Methoxy-1,2-diphenylethanone 12 was identified by comparison of its NMR data with those obtained from a commercial sample (Aldrich).
79. (a) Kloetzel, M. C. J. Am. Chem. Soc. 1940, 62, 1708.
80. (b) Dauben, W. G.; Tilles, H. J. Org. Chem. 1950, 15, 785.
81. (a) Reissig, H.-U.; Wienand, A. Angew. Chem., Int. Ed. Engl. 1990, 29, 1129.
82. (b) Reissig, H.-U.; Buchert, M.; Hoffmann, M. Chem. Ber. 1995, 128, 605.