Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: an entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction |
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Authors: | Nakao Yoshiaki Imanaka Hidekazu Sahoo Akhila K Yada Akira Hiyama Tamejiro |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan. nakao@npc05.kuic.kyoto-u.ac.jp |
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Abstract: | Alkenyl- and aryl2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. |
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