First gold complex-catalysed selective hydrosilylation of organic compounds

Chemical Communications

Volumn , Issue 11, 2000, Pages 981-982

  Ito, Hajime ^a   Yajima, Tatsuki ^b   Tateiwa, Jun Ichi ^b   Hosomi, Akira ^b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BENZALDEHYDE; CARBONYL DERIVATIVE; GOLD COMPLEX; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; REACTION ANALYSIS; REDUCTION;

EID: 0034616830     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001743o     Document Type: Article

References (17)

1. Y. Ito, M. Sawamura and T. Hayashi, J. Am. Chem. Soc., 1986, 108, 6405; Y. Fukuda and K. Utimoto, J. Org. Chem., 1991, 56, 3729; S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka, Gold Bull., 1996, 29, 131; Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma, J. Org. Chem., 1997, 62, 1594; J. H. Teles, S. Brode and M. Chabanas, Angew. Chem., Int. Ed., 1998, 37, 1415.
2. Y. Ito, M. Sawamura and T. Hayashi, J. Am. Chem. Soc., 1986, 108, 6405; Y. Fukuda and K. Utimoto, J. Org. Chem., 1991, 56, 3729; S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka, Gold Bull., 1996, 29, 131; Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma, J. Org. Chem., 1997, 62, 1594; J. H. Teles, S. Brode and M. Chabanas, Angew. Chem., Int. Ed., 1998, 37, 1415.
3. Y. Ito, M. Sawamura and T. Hayashi, J. Am. Chem. Soc., 1986, 108, 6405; Y. Fukuda and K. Utimoto, J. Org. Chem., 1991, 56, 3729; S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka, Gold Bull., 1996, 29, 131; Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma, J. Org. Chem., 1997, 62, 1594; J. H. Teles, S. Brode and M. Chabanas, Angew. Chem., Int. Ed., 1998, 37, 1415.
4. Y. Ito, M. Sawamura and T. Hayashi, J. Am. Chem. Soc., 1986, 108, 6405; Y. Fukuda and K. Utimoto, J. Org. Chem., 1991, 56, 3729; S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka, Gold Bull., 1996, 29, 131; Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma, J. Org. Chem., 1997, 62, 1594; J. H. Teles, S. Brode and M. Chabanas, Angew. Chem., Int. Ed., 1998, 37, 1415.
5. Y. Ito, M. Sawamura and T. Hayashi, J. Am. Chem. Soc., 1986, 108, 6405; Y. Fukuda and K. Utimoto, J. Org. Chem., 1991, 56, 3729; S. Komiya, T. Sone, Y. Usui, M. Hirano and A. Fukuoka, Gold Bull., 1996, 29, 131; Q. Xu, Y. Imamura, M. Fujiwara and Y. Souma, J. Org. Chem., 1997, 62, 1594; J. H. Teles, S. Brode and M. Chabanas, Angew. Chem., Int. Ed., 1998, 37, 1415.
6. For heterogeneous gold catalysts, see: J. E. Bailie and G. J. Hutchings, Chem. Commun., 1999, 2151 and references therein.
7. Comprehensive Handbook on Hydrosilylation, ed. B. Marciniec, Pergamon Press, New York, 1992; M. Hudlicky, Reductions in Organic Chemistry, American Chemical Society, Washington DC, 2nd edn., 1996; M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
8. Comprehensive Handbook on Hydrosilylation, ed. B. Marciniec, Pergamon Press, New York, 1992; M. Hudlicky, Reductions in Organic Chemistry, American Chemical Society, Washington DC, 2nd edn., 1996; M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
9. Comprehensive Handbook on Hydrosilylation, ed. B. Marciniec, Pergamon Press, New York, 1992; M. Hudlicky, Reductions in Organic Chemistry, American Chemical Society, Washington DC, 2nd edn., 1996; M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.
10. H. Ito, T. Yajima, J. Tateiwa and A. Hosomi, Tetrahedron Lett., 1999, 40, 7807.
11. C. A. McAuliffe, R. V. Parish and P. D. Randall, J. Chem. Soc., Dalton Trans., 1979, 1730.
12. It was reported that the reduction of a gold(I) complex with a hydride reagent gave metallic gold(0) and deeply colored gold clusters: K. P. Hall and D. M. P. Mingos, Prog. Inorg. Chem., 1984, 32, 237; G. Schmid, R. Pfeil, R. Boese, F. Bandermann, S. Meyer, G. H. M. Calis and J. W. A. van der Velden, Chem. Ber., 1981, 114, 3634.
13. It was reported that the reduction of a gold(I) complex with a hydride reagent gave metallic gold(0) and deeply colored gold clusters: K. P. Hall and D. M. P. Mingos, Prog. Inorg. Chem., 1984, 32, 237; G. Schmid, R. Pfeil, R. Boese, F. Bandermann, S. Meyer, G. H. M. Calis and J. W. A. van der Velden, Chem. Ber., 1981, 114, 3634.
14. 2) without acidic workup both 3a (30%) and 4a (58%) were obtained.
15. In the absence of a gold complex and tributylphosphine or in the presence of tributylphosphine alone as catalyst, no reaction was observed under the same conditions. See also ref. 3.
16. Although other hydrosilanes were also tested, use of phenyldimethylsilane 2 gave good results in most cases.
17. R. C. Larock, Comprehensive Organic Transformations, Wiley, New York, 2nd edn., 1999, pp. 1089-1096.