Trans-Hydrometalation of Alkynes by a Combination of InCl3 and DIBAL-H: One-Pot Access to Functionalized (Z)-Alkenes
- 23 July 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (17) , 2993-2995
- https://doi.org/10.1021/ol026401w
Abstract
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.Keywords
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