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Synthesis 2009(6): 963-968  
DOI: 10.1055/s-0028-1087802
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Iodine-Catalyzed Three-Component Reaction: A Rapid Synthesis of α-Alkoxy Azides and Homoallyl Ethers

Jhillu S. Yadav*, Basi V. Subba Reddy, Ganapuram Madhusudhan Reddy, Ravirala Narender
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 13 November 2008
Publication Date:
11 February 2009 (online)

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Abstract

Iodine is found to be an efficient catalyst for the three-component coupling of aldehydes, alcohols, and TMSN3 under mild and neutral conditions to provide α-alkoxy azides in good yields and with high selectivity. Allyltrimethylsilane also reacts rapidly with aldehydes in the presence of alcohols to produce homoallyl ethers under similar conditions. The use of iodine makes this procedure simple, convenient and cost-effective.

Key words

three-component reaction - molecular iodine - α-alkoxy azides - homoallylic ethers

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