4.4 Article

Synthesis of 1-haloethenamides from ynamide through halotrimethylsilane-mediated hydrohalogenation

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 3, Pages 632-635

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.11.091

Keywords

1-Haloethenamide; exo-Methylene; Vinyl halide; Hydrohalogenation

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convenient synthesis of 1-haloethenamides has been achieved by utilizing halotrimethylsilane (TMSX, X = Cl, Br, I) and water. Halotrimethylsilane in 1 M CH2-Cl-2 solution functions as a halogen source of the in situ generated HX, and the HX added to the terminal triple bonds of ynamides in Markovnikov fashion. (C) 2013 Elsevier Ltd. All rights reserved.

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