Alkyne Coupling Reactions Mediated by Organolanthanides. Probing the Mechanism by Metal and Alkyne Variation

Organometallics

Volumn 12, Issue 9, 1993, Pages 3618-3623

  Forsyth, Craig M ^a   Nolan, Steven P ^a   Stern, Charlotte L ^a   Marks, Tobin J ^a   Rheingold, Arnold L ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000440816     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00033a038     Document Type: Article

References (27)

1. For some examples involving olefins and acetylenes, see: Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123–3125.
2. Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980–1986 and references therein.
3. Heeres, H. J.; Meetsma, A.; Teuben, J. H.; Rogers, R. D. Organometallics 1989, 8, 2637–2646.
4. Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091–8103.
5. Jeske, G.; Schock, L. E.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103–8110.
6. Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111–8118.
7. Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51–55.
8. Manriquez, J. M.; Fagan, P. J.; Marks, T. J.; Vollmer, S. H.; Day, C. S.; Day, V. W. J. Am. Chem. Soc. 1979, 101, 5075–5078.
9. Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844–7853 and references therein.
10. Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115–4119.
11. Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709–714.
12. Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710–712.
13. CCR mode could not be detected in a bona fide lanthanide acetylide complex, see: Evans, W. J.; Ulibarri, T. A.; Chamberlain, L. R.; Ziller, J. W.; Alvarez, D. A., Jr. Organometallics 1990, 9, 2124–2130.
14. Evans, W. J.; Keyer, R. A.; Zhang, H.; Atwood, J. L. J. Chem. Soc., Chem. Commun. 1987, 837–838.
15. Evans, W. J.; Keyer, R. A.; Ziller, J. W. Organometallics 1990, 9, 2628–2631.
16. Sekutowski, D. G.; Stucky, G. D. J. Am. Chem. Soc. 1976, 98, 1376–1382.
17. See also: Cuenca, T.; Gomez, R.; Gomez-Sal, P.; Rodriguez, G. M.; Royo, P. Organometallics 1992, 11, 1229–1234 and references therein.
18. Moras, L. R. Chem. Rev. 1976, 76, 827–842.
19. 2Ln(THF)CCPh complexes (Ln = Ce, Nd) are also reported to yield coupling products under unspecified conditions.
20. Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115–4119.
21. Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307–312.
22. Shannon, R. D. Acta Crystallogr. 1976, A32, 751–767.
23. van der Heijden, H.; Schaverien, C. J.; Orpen, A. G. Organometallics 1989, 8, 255–258.
24. Scholz, A.; Smola, A.; Scholz, J.; Loebel, J.; Schumann, H.; Thiele, K. H. Angew. Chem., Int. Ed. Engl. 1991, 30, 435–436.
25. Fischer, R. D. In Organometallics of the f-Elements; Marks, T. J., Fischer, R. D., Eds.; Reidel: Dordrecht, The Netherlands, 1979; Chapter 11.
26. Fischer, R. D. In Fundamental and Technological Aspects of Organo-f-Element Chemistry; Marks, T. J., Fragala, I. L., Eds.; Reidel: Dordrecht, The Netherlands, 1985; Chapter 8.
27. Bertini, I.; Luchinat, C. NMR of Paramagnetic Molecules in Biological Systems, Benjamin: Menlo Park, CA, 1986; Chapter 10.