Journal
TETRAHEDRON LETTERS
Volume 50, Issue 6, Pages 640-643Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.11.083
Keywords
Henry reaction; Michael addition; Ionic liquids; Nitroalkanes; Carbonitriles; Thiocyanates
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A novel and convenient three-component coupling reaction of nitromethane, aromatic aldehydes and trimethylsilyl cyanide (TMSCN) or ammonium thiocyanate has been developed for an expeditious synthesis of beta-nitrocarbonitriles or beta-nitrothiocyanates, respectively, via C-C and C-S bond-forming reactions. The synthetic protocol strategically involves a one-pot sequential Henry reaction and a Michael addition efficiently promoted by the same ionic liquid [bmim]OH. The main advantages of the present approach include the use of inexpensive simple substrates and an ionic liquid as an efficient reaction promoter for the mild synthesis in a one-pot procedure. (C) 2008 Elsevier Ltd. All rights reserved.
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