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DOI: 10.1055/s-0035-1561487
Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications
Publication History
Received: 20 May 2016
Accepted after revision: 08 June 2016
Publication Date:
22 July 2016 (online)
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Dedicated to the memory of Jean-François Normant, an outstanding scientist and artist
Abstract
Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.
Key words
hydrosilylation - hydrostannylation - hydrogermylation - trifluoromethylated alkynes - trifluoromethylated alkenes - fluorinated probes - natural productsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561487.
- Supporting Information
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