Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate

Peter W. Anzalone, Ashvin R. Baru, Eric M. Danielson, Patrick D. Hayes, Mai P. Nguyen, Ambrose F. Panico, Russell C. Smith, Ram S. Mohan

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57 Scopus citations

Abstract

(Chemical Equation Presented) Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)3• xH 2O (1 < x < 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by in situ generation of the acetal followed by its reaction with allyltrialkylsilane or by a three-component synthesis in which the aldehyde, trimethylorthoformate or an alkoxytrimethylsilane and allyltrimethylsilane are mixed together in the presence of bismuth inflate (0.1-1.0 mol %). In addition, a three-component synthesis of homoallyl acetates, which is achieved by reacting the aldehyde, acetic anhydride, and allyltrimethylsilane in the presence of bismuth triflate (3.0-5.0 mol %), has been developed. The use of a relatively nontoxic, easy to handle, and inexpensive catalyst adds to the versatility of these methods.

Original languageEnglish (US)
Pages (from-to)2091-2096
Number of pages6
JournalJournal of Organic Chemistry
Volume70
Issue number6
DOIs
StatePublished - Mar 18 2005
Externally publishedYes

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