Intramolecular cyanoboration of alkynes via activation of boron-cyanide bonds by transition metal catalysts |
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Authors: | Michinori Suginome Akihiko Yamamoto Masahiro Murakami |
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Institution: | Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan |
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Abstract: | Cyano(dialkylamino)boryl ethers of homopropargylic alcohols undergo intramolecular addition of a B-CN bond across their carbon-carbon triple bonds (cyanoboration) in the presence of palladium and nickel catalysts, furnishing five-membered cyclic boryl ethers regioselectively in good yields via 5-exo cyclization. The products were transformed into highly substituted α,β-unsaturated nitriles via Suzuki-Miyaura coupling to aryl iodides, rhodium-catalyzed conjugative addition to methyl vinyl ketone, and rhodium-catalyzed protodeborylation. |
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Keywords: | Borylation Cyanation Cyanoborane Addition Palladium Nickel |
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