Trans-hydrometalation of alkynes by a combination of InCl3 and DIBAL-H: one-pot access to functionalized (Z)-alkenes |
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Authors: | Takami Kazuaki Yorimitsu Hideki Oshima Koichiro |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. |
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Abstract: | reaction: see text] Triethylborane-induced hydrometalation of alkynes proceeds in an anti manner to afford the corresponding (Z)-alkenylmetal compounds stereoselectively, where dichloroindium hydride would play a key role. A variety of functional groups including hydroxy, carbonyl, and carboxy groups were tolerant under the reaction conditions. Following iodolysis and cross-coupling reaction of the (Z)-alkenylmetal species show the usefulness of this strategy. |
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