Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases

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• 作者：Lothar W. Bieber ; Margarete F. da Silva
• 关键词：Allylation ; Functionalized alkynes ; Aprotic solvent ; Inorganic bases ; Selectivity
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：1 October 2007
• 卷：48
• 期：40
• 页码：7088-7090
• 文件大小：98 K

摘要

Allylic halides and terminal alkynes couple under CuI catalysis in DMSO or DMF solution. In most cases, sodium carbonate or bicarbonate is sufficient to promote the reaction; less reactive alkynes require catalytic amounts of DBU. Bifunctional alkynes and halides can be reacted selectively according to the stoichiometry used. Trimethylsilyl, hydroxyl, ester and halide groups are tolerated in the alkyne. Most halides react without allylic rearrangement. The method is suitable for the synthesis of functionalized enynes.