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Synlett 2010(10): 1515-1518
DOI: 10.1055/s-0029-1219944
DOI: 10.1055/s-0029-1219944
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Selective Propargylation of Azo Compounds with Barium Reagents
Further Information
Publication History
Received
10 March 2010
Publication Date:
25 May 2010 (online)


Abstract
A Barbier-type propargylation of azo compounds with γ-trialkylsilylated propargylic bromides has been achieved using reactive barium as a low-valent metal in THF. Corresponding propargylated hydrazines (α-adducts) were exclusively formed not only from azobenzenes (diaryldiazenes) but also from dialkyl azodicarboxylates. This method is also applicable to γ-alkylated or γ-phenylated propargylic bromides, providing the desired propargylated products only.
Key words
azo compounds - barium - hydrazine - propargylation - propargylic bromides