Iridium-catalyzed addition of acid chlorides to terminal alkynes

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作者
Iwai, Tomohiro [1 ]
Fujihara, Tetsuaki [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
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[1] Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
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(Chemical Equation Presented) An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-β-chloro-α,β- unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans. Copyright © 2009 American Chemical Society;
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页码:6668 / 6669
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