Reaction of Fischer carbene complexes with 1,3-butadiynes: A new strategem for biaryl synthesis with construction of the biaryl bond preceding synthesis of the arenes

Journal of the American Chemical Society

Volumn 118, Issue 9, 1996, Pages 2166-2181

  Bao, Jianming ^a   Wulff, William D ^a   Fumo, Michael J ^a   Grant, Eugene B ^a   Heller, Douglas P ^a   Whitcomb, Mark C ^a   Yeung, Siu Man ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BICYCLO COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029912555     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953146k     Document Type: Article

References (41)

1. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes: Verlag Chemie: Deerfield Beach, FL, 1984. (b) Dötz, K. H., Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, UK. 1990: Vol 5. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (g) Doyle, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12.
2. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes: Verlag Chemie: Deerfield Beach, FL, 1984. (b) Dötz, K. H., Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, UK. 1990: Vol 5. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (g) Doyle, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12.
3. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes: Verlag Chemie: Deerfield Beach, FL, 1984. (b) Dötz, K. H., Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, UK. 1990: Vol 5. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (g) Doyle, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12.
4. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes: Verlag Chemie: Deerfield Beach, FL, 1984. (b) Dötz, K. H., Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, UK. 1990: Vol 5. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (g) Doyle, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12.
5. For reviews on the synthetic applications of Fischer carbene complexes, see: (a) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes: Verlag Chemie: Deerfield Beach, FL, 1984. (b) Dötz, K. H., Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (c) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.; Greenwich, CT, 1989; Vol. 1. (d) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: Oxford, UK. 1990: Vol 5. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (f) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12. (g) Doyle, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12.
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31. Several intermolecular examples have been described since the original report by Fischer: (a) Fischer, E. O.; Heckel, B.; Dötz, K. H.; Muller, J.; Merner, H. J. J. Organomet. Chem. 1969, 16, P29. For intermolecular examples, see: (b) Huy, H. T.; Lefloch, P.; Louis, J. M.; Fetizon, M. J. Organomet. Chem. 1986, 311, 79. (c) Macomber, D. W.; Hung, M. H.; Verma A. G. Organometallics 1988, 7, 2072.
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