The interrupted Pauson-Khand reaction

Journal of the American Chemical Society

Volumn 118, Issue 25, 1996, Pages 6080-6081

  Krafft, M E ^a   Wilson, A M ^a   Dasse, O A ^a   Shao, B ^a   Cheung, Y Y ^a   Fu, Z ^a   Bonaga, L V R ^a   Mollman, M K ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030018444     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9606541     Document Type: Article

References (39)

1. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. E. J. Chem. Soc., Perkin Trans. 1 1973, 977. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans, 1 1973, 975.
2. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. E. J. Chem. Soc., Perkin Trans. 1 1973, 977. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans, 1 1973, 975.
3. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1037. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry- II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
4. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1037. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry- II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
5. Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1037. Schore, N. E. Org. React. 1991, 40, 1. Schore, N. E. In Comprehensive Organometallic Chemistry- II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703.
6. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E. Synlett 1991, 204. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
7. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E. Synlett 1991, 204. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
8. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E. Synlett 1991, 204. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
9. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
10. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
11. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
12. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
13. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
14. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
15. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
16. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
17. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
18. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
19. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
20. Zr: Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593 and references cited therein. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 5, pp 1163-1184. W: Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. Ti: Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261 and references cited therein. Fe: Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. Rh: Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1989, 29, 6421. Anastasiou, D.; Jackson, W. R. Tetrahedron Lett. 1990, 31, 4795. Ni: Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433. Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moreto, J. M. J. Am. Chem. Soc. 1992, 114, 10449. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. Pd: Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38.
21. For examples, see: Kablauoni, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787 and references cited therein.
22. For examples, see: Kablauoni, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787 and references cited therein.
23. For representative examples, see: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
24. For representative examples, see: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
25. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Schore, N. E. Chem. Rev. 1988, 88, 1081.
26. Trost, B. M. Acc. Chem. Res. 1990, 23, 34. Schore, N. E. Chem. Rev. 1988, 88, 1081.
27. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791.
28. Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133.
29. Matsunaga, P. T.; Hillhouse, G. L. J. Am. Chem. Soc. 1993, 115, 2075.
30. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
31. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
32. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
33. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
34. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
35. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
36. For representative oxidations of M-C bonds, see the following. C-Zn: Klement, I.; Lutjens, H.; Knochel, P. Tetrahedron Lett. 1995, 36, 3161. C-Ni: Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133. C-Pd: Kitching, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, UK, 1991; Vol. 7, pp 613-639. C-Al: Negishi, E-i.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. Insertions that yield a π-allyl metal complex can be functionalized by nucleophilic addition to give C-N, C-O, or C-C bonds; for examples, see: Grigg, R.; Dorrity, M. J.; Malone, J. F. Tetrahedron Lett. 1990, 31, 1343. Takacs, J. M.; Zhu, J. J. Org. Chem. 1989, 54, 5193. C-Ti: Wilson, A. M.; West, F. G.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 1995, 117, 8490.
37. 2, 100.
38. 1,3-Dienes have frequently been observed as byproducts from the thermal Pauson-Khand cycloaddition. 1,3-Dienes are the only product formed when electron-deficient alkenes are used. See: Khand, I. U.; Pauson, P. L. J. Chem. Soc., Chem. Commun. 1974, 379.
39. Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851.