Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes
Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes
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DOI：
10.1021/jo500464q
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发表时间：
2014-05-02
影响因子：
3.6
通讯作者：
Ryu, Ilhyong
中科院分区：
文献类型：
--
作者：
Kawamoto, Takuji;Uehara, Shohei;Ryu, Ilhyong
氰基硼氢化物是碘代烷与缺电子烯烃还原加成反应的有效试剂。与使用锡试剂相反，反应在碳-碘键处而不是在碳-溴或碳-氯键处化学选择性地发生。该反应体系已成功应用于自由基羰基化等三组分反应。从氰基硼氢化四丁基铵中提取伯烷基的氢的速率常数估计为
Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be