Sequential Protocol for C(sp3)-H Carboxylation with CO2: Transition-Metal-Catalyzed Benzylic C-H Silylation and Fluoride-Mediated Carboxylation
Sequential Protocol for C(sp3)-H Carboxylation with CO2: Transition-Metal-Catalyzed Benzylic C-H Silylation and Fluoride-Mediated Carboxylation
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DOI：
10.1021/ol301431d
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发表时间：
2012-07-06
期刊：
影响因子：
5.2
通讯作者：
Sato, Yoshihiro
中科院分区：
文献类型：
--
作者：
Mita, Tsuyoshi;Michigami, Kenichi;Sato, Yoshihiro
目前有机化学中最具挑战性的转化之一是使用廉价且普遍存在的Cl源CO2气体催化C（sp（3））-H键的羧化。建立了一种连续的C（sp（3））-H羧化反应方案，该方案采用氮导向、金属辅助的C-H活化/催化硅烷化反应结合氟化物介导的CO2羧化反应。羧化反应只在苄基C（sp（3））-Si键上进行，而不在芳香C（sp（2））-Si键上进行，这有利于产物的进一步操作。
One of the most challenging transformations in current organic chemistry is the catalytic carboxylation of a C(sp(3))-H bond using CO2 gas, an inexpensive and ubiquitous Cl source. A sequential protocol for C(sp(3))-H carboxylation by employing a nitrogen-directed, metal-assisted, C-H activation/catalytic silylation reaction in conjunction with fluoride-mediated carboxylation with CO2 was established. The carboxylation proceeded only at the benzylic C(sp(3))-Si bond, not at the aromatic C(sp(2))-Si, which is advantageous for further manipulations of the products.