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Synthesis 2005(13): 2129-2136  
DOI: 10.1055/s-2005-870010
PAPER
© Georg Thieme Verlag Stuttgart · New York

RuCl3 in Poly(ethylene glycol): A Highly Efficient and Recyclable Catalyst for the Conjugate Addition of Nitrogen and Sulfur Nucleophiles

Huaxing Zhanga,b, Yuhong Zhang*a, Leifang Liua, Hailiang Xua, Yanguang Wang*a
a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
Fax: +86(71)7951512; e-Mail: yhzhang@zjuem.zju.edu.cn; e-Mail: orgwyg@zju.edu.cn;
b Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, P. R. China
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Publikationsverlauf

Received 21 January 2005
Publikationsdatum:
13. Juli 2005 (online)

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Abstract

The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls.

Key words

RuCl3 - PEG - amines - thiols - conjugate addition