3 years ago

Highly Selective Olefin-Assisted PdII-Catalyzed Oxidative Alkynylation of Enallenes

Highly Selective Olefin-Assisted PdII-Catalyzed Oxidative Alkynylation of Enallenes
Jan-E. Bäckvall, Youai Qiu, Bin Yang, Jeffrey L. Henry, Daniels Posevins
An olefin-assisted, palladium-catalyzed oxidative alkynylation of enallenes for regio- and stereoselective synthesis of substituted trienynes has been developed. The reaction shows a broad substrate scope and good tolerance for various functional groups on the allene moiety, including carboxylic acid esters, free hydroxyls, imides, and alkyl groups. Also, a wide range of terminal alkynes with electron-donating and electron-withdrawing aryls, heteroaryls, alkyls, trimethylsilyl, and free hydroxyl groups are tolerated. Highly selective palladium-catalyzed oxidative alkynylation of enallenes has been developed, affording regio- and stereoselectively substituted trienynes. The reaction shows a broad substrate scope with good tolerance for various functional groups on the enallene and the terminal alkyne.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701654

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