4.4 Article

InX3-catalyzed haloamidation of vinyl arenes: a facile synthesis of α-bromo- and α-fluoroamides

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 10, Pages 1136-1138

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.090

Keywords

Indium(III) halides; Vinyl arenes; Haloamidation; alpha-Fluoroamides

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A variety of alkenes are converted into the corresponding alpha-fluoroamides in high yields by selectfluor (TM) in the presence of 10 mol % of InF3 in nitrile solution. alpha-Bromoamides are obtained with NBS in the presence of 10 mol % InBr3 under similar conditions. The use of Lewis acid in haloamidation significantly improved the yields and reaction rates. (C) 2009 Elsevier Ltd. All rights reserved.

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