Journal
TETRAHEDRON
Volume 70, Issue 35, Pages 5843-5848Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.06.037
Keywords
Sonogashira cross-coupling; 3-Bromo-1,2-dione; 3-Alkynyl-1,2-dione
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Funding
- Estonian Ministry of Education and Research [YUT 19-32, ETF 8880]
- EU European Regional Development Fund [3.2.0101.08-0017]
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A new general method for the synthesis of enols of cyclic 3-alkynyl-substituted 1,2-diketones is developed. Sonogashira cross-coupling of silyl enolates of cyclic 3-bromo-cyclopentane- and 3-bromo-cyclohexane-1,2-diones with variety of substituted acetylenes afforded enols of cyclic 3-alkynyl-1,2-diones with good yields (up to 93%) in a short reaction time. The starting 3-bromo-1,2-diones are easily obtainable by direct bromination of 1,2-diones with NBS. (C) 2014 Elsevier Ltd. All rights reserved.
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