Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters

Journal of the American Chemical Society

Volumn 118, Issue 39, 1996, Pages 9440-9441

  Parks, Daniel J ^a   Piers, Warren E ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSILICON DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029952124     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961536g     Document Type: Article

References (29)

1. (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989.
2. (b) Marciniec, B. Comprehensive Handbook on Hydrosilation; Pergamon: New York, 1992.
3. Boyer, J.; Breliere, C.; Corriu, R. J. P.; Kpoton, A.; Poirier, M.; Royo, G. J. Organomet. Chem. 1986, 311, C39.
4. Corriu, R. J. P.; Perz, R., Reye, C. Tetrahedron 1983, 39, 999.
5. Calas, R. Pure Appl. Chem. 1966, 13, 61.
6. (a) Fry, J. L.; Orfanopoulo, M.; Adlington, M. G.; Dittman, W. R.; Silverman, S. B. J. Org. Chem. 1978, 43, 374.
7. (b) Doyle, M. P.; West, C. T.; Donnelly, S. J.; McOsker, C. C. J. Organomet. Chem. 1976, 117, 129 and other papers in this series.
8. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1966, 5, 218.
9. (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
10. (b) Ewen, J. A.; Edler, M. J. Canadian Patent App 2,027,145, 1991; Chem. Abstr. 1991, 115, 136998g.
11. (a) Ishihara, K.; Hananki, N.; Yamamoto, H. Synlett. 1993, 577.
12. (b) Ishihara, K.; Funahasi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
13. (c) Ishihara, K.; Hananki, N.; Yamamoto, H. Synlett 1995, 721.
14. (d) Ishihara, K.; Hanaki, N.; Funahasi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
15. See supporting information for further details.
16. -1, 203 K.
17. 1H NMR according to: Drago, R. S. Physical Methods for Chemists, 2nd ed.; Saunders: New York, 1992; p 257.
18. -1.
19. Maria, P.-C.; Gal, J.-F. J. Phys. Chem. 1985, 89, 1296.
20. Structurally characterized adducts of boron Lewis acids with carbonyl compounds are rare: (a) Corey, E. J.; Loh, T.-P.; Sarshar, S.; Azimioara, M. Tetrahedron Lett. 1992, 33, 6945. (b) Reetz, M. T.; Hüllmann, M.; Massa, W.; Berger, S.; Radmacher, P.; Heymanns, P. J. Am. Chem. Soc., 1986, 108, 2405.
21. Structurally characterized adducts of boron Lewis acids with carbonyl compounds are rare: (a) Corey, E. J.; Loh, T.-P.; Sarshar, S.; Azimioara, M. Tetrahedron Lett. 1992, 33, 6945. (b) Reetz, M. T.; Hüllmann, M.; Massa, W.; Berger, S.; Radmacher, P.; Heymanns, P. J. Am. Chem. Soc., 1986, 108, 2405.
22. The structures of 1-H, 1-Me, 1-OEt will be published elsewhere; spectroscopic details and ORTEP diagrams are included as supporting information.
23. There is a well-documented electronic preference for Lewis acids to bind carbonyl lone pairs trans to electron donating groups. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256.
24. These plots were linear for only 3-4 half-lives for ester reductions, at which point the observed rate of silane consumption declined. We believe this is due to a poisoning of the reaction due to production of small amounts of aldehydes (vide infra).
25. 3SiH] vs time were nonlinear.
26. 1.
27. 3[substrate]).
28. 2, arguing against such a stepwise process.
29. eq for eq 1, transition state effects may reinforce observed reactivity trends.