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

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2002(6): 0717-0719
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;

Further Information

Publication History

Received 15 February 2002
Publication Date:
26 April 2002 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

References

1a Tamao K. Kobayashi K. Ito Y. Tetrahedron Lett. 1989, 30: 6051

Google Scholar
1b Shibata K. Miyazawa K. Goto Y. Chem. Commun. 1997, 1309

Google Scholar
1c Mowery ME. DeShong P. J. Org. Chem. 1999, 64: 1684

Google Scholar
1d Mowery ME. DeShong P. Org. Lett. 1999, 1: 2140

Google Scholar
1e Lee HM. Nolan SP. Org. Lett. 2000, 2: 2053

Google Scholar
2a Lam PYS. Deudon S. Averill KM. Li R. He MY. DeShong P. Clark CG. J. Am. Chem. Soc. 2000, 122: 7600

Crossref Google Scholar
2b Lam PYS. Deudon S. Hauptman E. Clark CG. Tetrahedron Lett. 2001, 42: 2427

Crossref Google Scholar
3 Murata M. Shimazaki R. Watanabe S. Masuda Y. Synthesis 2001, 2231

Article in Thieme Connect Google Scholar
4a Oi S. Moro M. Inoue Y. Chem. Commun. 1997, 1621

Crossref Google Scholar
4b Oi S. Moro M. Ono S. Inoue Y. Chem. Lett. 1998, 83

Crossref Google Scholar
4c Oi S. Moro M. Fukuhara H. Kawanishi H. Inoue Y. Tetrahedron Lett. 1999, 40: 9259

Crossref Google Scholar
5a Sakai M. Hayashi H. Miyaura N. Organometallics 1997, 16: 4229

Crossref Google Scholar
5b Sakai M. Ueda M. Miyaura N. Angew. Chem., Int. Ed. 1998, 37: 3279

Crossref Google Scholar
5c Ueda M. Miyaura N. J. Organomet. Chem. 2000, 595: 31

Crossref Google Scholar
6 Oi S. Moro M. Inoue Y. Organometallics 2001, 20: 1036

Crossref Google Scholar
7 Fujii T. Koike T. Mori A. Osakada K. Synlett 2002, 298

Article in Thieme Connect Google Scholar
8 Huang TS. Li CJ. Chem. Commun. 2001, 2348

Crossref Google Scholar
9a Mori A. Danda Y. Fujii T. Hirabayashi K. Osakada K. J. Am. Chem. Soc. 2001, 123: 10774

Article in Thieme Connect Google Scholar
9b Koike T. Du X. Mori A. Osakada K. Synlett 2002, 301

Article in Thieme Connect Google Scholar
9c Fujii T. Koike T. Mori A. Osakada K. Synlett 2002, 295

Article in Thieme Connect Google Scholar
10 Oi S. Honma Y. Inoue Y. Org. Lett. 2002, 4: 669

Google Scholar
11a Murata M. Suzuki K. Watanabe S. Masuda Y. J. Org. Chem. 1997, 62: 8569

Google Scholar
11b Murata M. Watanabe S. Masuda Y. Tetrahedron Lett. 1999, 40: 9255

Google Scholar
11c Manoso AS. DeShong P. J. Org. Chem. 2001, 66: 7455

Google Scholar
12a Usón R. Oro LA. Cabeza JA. Inorg. Synth. 1985, 23: 126

Google Scholar
12b Agarawal SK. Mehrotra RC. J. Indian Chem. Soc. 1985, 62: 805

Google Scholar
13a Hatanaka Y. Hiyama T. Synlett 1991, 845

Article in Thieme Connect Google Scholar
13b Hiyama T. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinhein: 1998. p.421

Article in Thieme Connect Google Scholar