Rhodium(I)-Catalyzed 1,2- and 1,4-Addition of Aryltriethoxysilanes to Carbonyl Compounds under Aqueous Basic Conditions

Miki Murata; Ryuta Shimazaki; Masanori Ishikura; Shinji Watanabe; Yuzuru Masuda

doi:10.1055/s-2002-25764

SHORTPAPER

Rhodium(I)-Catalyzed 1,2- and 1,4-Addition of Aryltriethoxysilanes to Carbonyl Compounds under Aqueous Basic Conditions

Miki Murata*, Ryuta Shimazaki, Masanori Ishikura, Shinji Watanabe, Yuzuru Masuda*
Department of Materials Science, Kitami Institute of Technology, Kitami, 090-8507, Japan
Fax: +81(157)264973; e-Mail: muratamk@mail.kitami-it.ac.jp; e-Mail: masudayz@mail.kitami-it.ac.jp;

Abstract

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Abstract

Aryltriethoxysilanes add to aldehydes and α,β-unsaturated carbonyl compounds in high yield in the presence of a rhodium(I) catalyst and aqueous sodium hydroxide.

Key words

rhodium - addition reactions - silicon - arylations - carbonyl compounds

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References

<A NAME="RF01902SS-1A">1a</A> Tamao K. Kobayashi K. Ito Y. Tetrahedron Lett. 1989, 30: 6051

<A NAME="RF01902SS-1B">1b</A> Shibata K. Miyazawa K. Goto Y. Chem. Commun. 1997, 1309

<A NAME="RF01902SS-1C">1c</A> Mowery ME. DeShong P. J. Org. Chem. 1999, 64: 1684

<A NAME="RF01902SS-1D">1d</A> Mowery ME. DeShong P. Org. Lett. 1999, 1: 2140

<A NAME="RF01902SS-1E">1e</A> Lee HM. Nolan SP. Org. Lett. 2000, 2: 2053

<A NAME="RF01902SS-2A">2a</A> Lam PYS. Deudon S. Averill KM. Li R. He MY. DeShong P. Clark CG. J. Am. Chem. Soc. 2000, 122: 7600

<A NAME="RF01902SS-2B">2b</A> Lam PYS. Deudon S. Hauptman E. Clark CG. Tetrahedron Lett. 2001, 42: 2427

<A NAME="RF01902SS-3">3</A> Murata M. Shimazaki R. Watanabe S. Masuda Y. Synthesis 2001, 2231

<A NAME="RF01902SS-4A">4a</A> Oi S. Moro M. Inoue Y. Chem. Commun. 1997, 1621

<A NAME="RF01902SS-4B">4b</A> Oi S. Moro M. Ono S. Inoue Y. Chem. Lett. 1998, 83

<A NAME="RF01902SS-4C">4c</A> Oi S. Moro M. Fukuhara H. Kawanishi H. Inoue Y. Tetrahedron Lett. 1999, 40: 9259

<A NAME="RF01902SS-5A">5a</A> Sakai M. Hayashi H. Miyaura N. Organometallics 1997, 16: 4229

<A NAME="RF01902SS-5B">5b</A> Sakai M. Ueda M. Miyaura N. Angew. Chem., Int. Ed. 1998, 37: 3279

<A NAME="RF01902SS-5C">5c</A> Ueda M. Miyaura N. J. Organomet. Chem. 2000, 595: 31

<A NAME="RF01902SS-6">6</A> Oi S. Moro M. Inoue Y. Organometallics 2001, 20: 1036

<A NAME="RF01902SS-7">7</A> Fujii T. Koike T. Mori A. Osakada K. Synlett 2002, 298

<A NAME="RF01902SS-8">8</A> Huang TS. Li CJ. Chem. Commun. 2001, 2348

<A NAME="RF01902SS-9A">9a</A> Mori A. Danda Y. Fujii T. Hirabayashi K. Osakada K. J. Am. Chem. Soc. 2001, 123: 10774

<A NAME="RF01902SS-9B">9b</A> Koike T. Du X. Mori A. Osakada K. Synlett 2002, 301

<A NAME="RF01902SS-9C">9c</A> Fujii T. Koike T. Mori A. Osakada K. Synlett 2002, 295

<A NAME="RF01902SS-10">10</A> Oi S. Honma Y. Inoue Y. Org. Lett. 2002, 4: 669

<A NAME="RF01902SS-11A">11a</A> Murata M. Suzuki K. Watanabe S. Masuda Y. J. Org. Chem. 1997, 62: 8569

<A NAME="RF01902SS-11B">11b</A> Murata M. Watanabe S. Masuda Y. Tetrahedron Lett. 1999, 40: 9255

<A NAME="RF01902SS-11C">11c</A> Manoso AS. DeShong P. J. Org. Chem. 2001, 66: 7455

<A NAME="RF01902SS-12A">12a</A> Usón R. Oro LA. Cabeza JA. Inorg. Synth. 1985, 23: 126

<A NAME="RF01902SS-12B">12b</A> Agarawal SK. Mehrotra RC. J. Indian Chem. Soc. 1985, 62: 805

<A NAME="RF01902SS-13A">13a</A> Hatanaka Y. Hiyama T. Synlett 1991, 845

<A NAME="RF01902SS-13B">13b</A> Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinhein: 1998. p.421