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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 435-440

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: Tetraorganosilanes for the practical cross-coupling reaction

Yoshiaki Nakao, Akhila K. Sahoo, Hidekazu Imanaka, Akira Yada and Tamejiro Hiyama

Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan

Abstract: Readily accessible and highly stable alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes cross-couple with various aryl and alkenyl halides under mild reaction conditions employing K2CO3 as a base at 35-80 °C. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue, cyclic silyl ether, is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinated silicates having a transferable group at an axial position.