Activation of silanes by Grubbs' carbene complex Cl2(PCy3)2Ru=CHPh: Dehydrogenative condensation of alcohols and hydrosilylation of carbonyls

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6363-6366

  Maifeld, Sarah V ^a   Miller, Reagan L ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBENOID; CARBONYL DERIVATIVE; ETHER DERIVATIVE; RUTHENIUM COMPLEX; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; HYDROGENATION; HYDROSILYLATION; REACTION ANALYSIS;

EID: 0037009701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01385-0     Document Type: Article

References (29)

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2. For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393; (d) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
3. For recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371; (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393; (d) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
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16. For examples of dehydrogenative condensations of alcohols and silanes, see: (a) Zhang, C.; Laine, R. M. J. Am. Chem. Soc. 2000, 122, 6979; (b) Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887 and references cited therein; (c) Ojima, I.; Kogure, T.; Nihonyangi, M.; Kono, H.; Inaba, S. Chem. Lett. 1973, 501.
17. For examples of dehydrogenative condensations of alcohols and silanes, see: (a) Zhang, C.; Laine, R. M. J. Am. Chem. Soc. 2000, 122, 6979; (b) Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887 and references cited therein; (c) Ojima, I.; Kogure, T.; Nihonyangi, M.; Kono, H.; Inaba, S. Chem. Lett. 1973, 501.
18. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
19. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
20. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
21. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
22. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
23. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
24. For examples of carbonyl hydrosilylation, see: (a) Chrisman, W.; Noson, K.; Lipshutz, B. H. J. Organomet. Chem. 2001, 624, 367; (b) Parks, D. J.; Blackwell, J. M.; Pier, W. E. J. Org. Chem. 2000, 65, 3090; (c) Bushell, S. M.; Lawrence, N. J. Tetrahedron Lett. 2000, 4507; (d) Lee, S.; Kim, T. Y.; Park, M. K.; Han, B. H. Bull. Korean Chem. Soc. 1996, 17, 1082; (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440; (f) Wang, D.; Chan, T. H. Tetrahedron Lett. 1993, 34, 3095; (g) Cornish, A. J.; Lappert, M. F.; Filatovs, G. L.; Nile, T. A. J. Organomet. Chem. 1979, 172, 153.
25. In some cases, a small amount of silyl byproduct was produced presumably from the dehydrocondensation of two silanes or the formation of siloxanes. However, for most cases, filtering the reaction through a short plug of silica to remove catalyst provides pure silyl ethers.
26. Only a few reports of carbonyl hydrolsilylation catalyzed by metal-carbene complexes exist in the literature. For rhodium(I) complexes, see: (a) Hill, J. E.; Nile, T. A. J. Organomet. Chem. 1977, 137, 293; (b) Herrmann, W. A.; Goosen, L. J.; Kocher, C.; Artus, C. R. Angew. Chem., Int. Ed. 1996, 35, 2805; (c) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70; (d) For rhodium(I) and ruthenium(II), see: Haskell, R. K.; Lappert, M. F. J. Organomet. Chem. 1984, 264, 217.
27. Only a few reports of carbonyl hydrolsilylation catalyzed by metal-carbene complexes exist in the literature. For rhodium(I) complexes, see: (a) Hill, J. E.; Nile, T. A. J. Organomet. Chem. 1977, 137, 293; (b) Herrmann, W. A.; Goosen, L. J.; Kocher, C.; Artus, C. R. Angew. Chem., Int. Ed. 1996, 35, 2805; (c) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70; (d) For rhodium(I) and ruthenium(II), see: Haskell, R. K.; Lappert, M. F. J. Organomet. Chem. 1984, 264, 217.
28. Only a few reports of carbonyl hydrolsilylation catalyzed by metal-carbene complexes exist in the literature. For rhodium(I) complexes, see: (a) Hill, J. E.; Nile, T. A. J. Organomet. Chem. 1977, 137, 293; (b) Herrmann, W. A.; Goosen, L. J.; Kocher, C.; Artus, C. R. Angew. Chem., Int. Ed. 1996, 35, 2805; (c) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70; (d) For rhodium(I) and ruthenium(II), see: Haskell, R. K.; Lappert, M. F. J. Organomet. Chem. 1984, 264, 217.
29. Only a few reports of carbonyl hydrolsilylation catalyzed by metal-carbene complexes exist in the literature. For rhodium(I) complexes, see: (a) Hill, J. E.; Nile, T. A. J. Organomet. Chem. 1977, 137, 293; (b) Herrmann, W. A.; Goosen, L. J.; Kocher, C.; Artus, C. R. Angew. Chem., Int. Ed. 1996, 35, 2805; (c) Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70; (d) For rhodium(I) and ruthenium(II), see: Haskell, R. K.; Lappert, M. F. J. Organomet. Chem. 1984, 264, 217.