Palladium-catalyzed C-H fluorosilylation of 2-phenylpyridines: synthesis of silafluorene equivalents.
Palladium-catalyzed C-H fluorosilylation of 2-phenylpyridines: synthesis of silafluorene equivalents.
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DOI：
10.1002/anie.201310293
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发表时间：
2014-03
影响因子：
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通讯作者：
Q. Xiao;Xiangtai Meng;M. Kanai;Y. Kuninobu
中科院分区：
文献类型：
--
作者：
Q. Xiao;Xiangtai Meng;M. Kanai;Y. Kuninobu
在钯催化下，用氨基(1,3,2-二氧硼杂硼烷-2-基)二苯基硅烷处理2-苯基吡啶，以良好至优异的收率产生氟硅烷化2-苯基吡啶。该反应是 C-H 氟硅烷化的第一个例子。单晶X射线结构分析表明硅原子和氮原子之间存在路易斯酸碱相互作用，所得氟硅烷化产物为硅芴等价物。氟硅烷化产物比相应的硅芴衍生物表现出更强的荧光。
Treatment of 2-phenylpyridines with amino(1,3,2-dioxaborolan-2-yl)diphenylsilane produced fluorosilylated 2-phenylpyridines in good to excellent yields under palladium catalysis. This reaction is the first example of C-H fluorosilylation. Single-crystal X-ray structure analysis revealed a Lewis acid-base interaction between the silicon and nitrogen atoms, and the obtained fluorosilylated products are silafluorene equivalents. The fluorosilylated products showed stronger fluorescence than the corresponding silafluorene derivative.