Tetrahedron Letters

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

LW Bieber, MF da Silva

Index: Bieber, Lothar W.; da Silva, Margarete F. Tetrahedron Letters, 2007 , vol. 48, # 40 p. 7088 - 7090

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Citation Number: 40

Abstract

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. ...