Palladium-Catalyzed Addition of Cyanoboranes to Alkynes: Regio- and Stereoselective Synthesis of α,β-Unsaturated β-Boryl Nitriles
Michinori Suginome Prof. Dr.
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
PRESTO, Japan Science and Technology Corporation, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorAkihiko Yamamoto
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
Search for more papers by this authorMasahiro Murakami Prof. Dr.
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
Search for more papers by this authorMichinori Suginome Prof. Dr.
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
PRESTO, Japan Science and Technology Corporation, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Search for more papers by this authorAkihiko Yamamoto
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
Search for more papers by this authorMasahiro Murakami Prof. Dr.
Kyoto University, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Fax: (+81) 75-383-2722
Search for more papers by this authorGraphical Abstract
Highly versatile intermediates are formed through the Pd-catalyzed cyanoboration of alkynes, which proceeds in a cis fashion. When 1-aryl alkynes are used, the corresponding α,β-unsaturated β-boryl nitriles are obtained regioselectively in good yields with the cyano group α to the aryl group. Suzuki–Miyaura coupling of the products leads to highly substituted α,β-unsaturated nitriles (see scheme).
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References
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