LiAl(OC(Ph)(CF3)2)4: A hydrocarbon-soluble catalyst for carbon-carbon bond-forming reactions

Organometallics

Volumn 15, Issue 18, 1996, Pages 3776-3778

  Barbarich, Thomas J ^a   Handy, Scott T ^b   Miller, Susie M ^a   Anderson, Oren P ^a   Grieco, Paul A ^b   Strauss, Steven H ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000825312     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9604031     Document Type: Article

References (29)

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6. For examples see the following and references therein: (a) Turner, H. W. European Patent Appl. 277,004 (assigned to Exxon), 1988. (b) Pellecchia, C.; Longo, P.; Proto, A.; Zambelli, A. Makromol. Chem., Rapid Commun. 1992, 13, 265. (c) Jia, L.; Yang, X.; Stern, C.; Marks, T. J. Organometallics 1994, 13, 3755. (d) Tjaden, E. B.; Swenson, D. C.; Jordan, R. F.; Peterson, J. L. Organometallics 1995, 14, 371.
7. For examples see the following and references therein: (a) Turner, H. W. European Patent Appl. 277,004 (assigned to Exxon), 1988. (b) Pellecchia, C.; Longo, P.; Proto, A.; Zambelli, A. Makromol. Chem., Rapid Commun. 1992, 13, 265. (c) Jia, L.; Yang, X.; Stern, C.; Marks, T. J. Organometallics 1994, 13, 3755. (d) Tjaden, E. B.; Swenson, D. C.; Jordan, R. F.; Peterson, J. L. Organometallics 1995, 14, 371.
8. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
9. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
10. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
11. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
12. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
13. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
14. For examples see the following and references therein: (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Grieco, P. A.; Cooke, R. J.; Henry, K. J.; VanderRoest, J. M. Tetrahedron Lett. 1991, 32, 4665. (c) DuBay, W. J.; Grieco, P. A.; Todd, L. J. J. Org. Chem. 1994, 59, 6898. (d) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem. Ber. 1994, 127, 1761. (e) Kobayashi, H.; Nie, J.; Sonoda, T. Chem. Lett. 1995, 307. (f) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104. (g) Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. Synlett 1995, 565.
15. Kirschner, E. M. Environment, Health Concerns Force Shift in Use of Organic Solvents. Chem. Eng. News 1994, June 20, p 13.
16. 14 are at least 41 and 32 mM, respectively.
17. 2) for all non-hydrogen atoms; hydrogen atoms in calculated positions; no absorption correction; final R(I > 2σ(I)) = 0.052, final R(all data) = 0.105; total number of parameters = 596.
18. 12,16]tricosa-12,14,-16(23)-triene.
19. Kulawiec, R. J.; Crabtree R. H. Coord. Chem. Rev. 1990, 99, 89.
20. Stalke, D.; Whitmire, K. H. J. Chem. Soc., Chem. Commun. 1990, 833.
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22. Wells, A. F. Structural Inorganic Chemistry, 5th ed.; Oxford University Press: Oxford, England, 1984; p 444.
23. 2 was employed in the reaction of cyclohexenone with silyl ketene acetal 2 in toluene, no reaction was observed.
24. + complex results in decreased reaction rates.
25. When hexamethylphosphoramide (HMPA) was employed in place of TMEDA in rxns 2 and 3, dramatically lower rates were observed: for example, substrate 5 required ca. 50 h in order to realize an 87% yield of 6.
26. (a) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1013.
27. (b) Bunce, R. A.; Schlecht, M. F.; Dauben, W. G.; Heathcock, C. H. Tetrahedron Lett. 1983, 24, 4943.
28. (a) Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 2986.
29. (b) Grieco, P. A.; Collins, J. L.; Henry, K. J. Tetrahedron Lett. 1992, 33, 4735.