Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding.
Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding.
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DOI：
10.1021/acs.orglett.5b01290
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发表时间：
2015-05
期刊：
影响因子：
5.2
通讯作者：
M. Saito;Nobuya Tsuji;Yusuke Kobayashi;Y. Takemoto
中科院分区：
文献类型：
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作者：
M. Saito;Nobuya Tsuji;Yusuke Kobayashi;Y. Takemoto
人们发现，卤键（XB）供体与三甲基卤化硅的组合使用是一种有效的助催化体系，可用于醇与各种亲核试剂（例如烯丙基三甲基硅烷和三甲基氰化物）的直接脱羟基偶联反应，以中等至优异的收率得到相应的加合物。详细的控制实验和机理研究表明，XB 相互作用对该反应至关重要。还描述了该偶联反应的应用。
The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.