Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction
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DOI：
10.1021/ja051281j
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发表时间：
2005-05-18
影响因子：
15
通讯作者：
Hiyama, T
中科院分区：
文献类型：
--
作者：
Nakao, Y;Imanaka, H;Hiyama, T
烯基-和芳基[2-(羟甲基)苯基]二甲基硅烷是高度稳定的四有机硅试剂，被发现在钯催化剂和K2CO3作为碱的存在下与芳基和烯基碘化物反应，与报道的硅基交叉偶联反应相比，反应条件明显更温和。该反应可耐受多种官能团，包括甲硅烷基保护剂，并允许进行克级合成以回收和再利用硅残留物。
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3as 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.