Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
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DOI：
10.1002/chem.201505106
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发表时间：
2016-03-14
影响因子：
4.3
通讯作者：
Feringa, Ben L.
中科院分区：
文献类型：
--
作者：
Heijnen, Dorus;Gualtierotti, Jean-Baptiste;Feringa, Ben L.
介绍了镍催化的芳香亲电试剂（溴化物、氯化物、氟化物和甲基醚）与有机锂试剂的选择性交叉偶联反应。市售镍N-杂环卡宾（NHC）络合物的使用允许与各种（杂）芳基锂化合物（包括经由金属-卤素交换或直接金属氢化制备的那些）反应，而市售富电子镍-双膦络合物将烷基锂物质顺利地转化成相应的偶联产物。这些反应在温和条件（室温）下快速进行（1小时），同时避免形成不期望的还原或均偶联产物。
Nickel-catalyzed selective cross-coupling of aromatic electrophiles (bromides, chlorides, fluorides and methyl ethers) with organolithium reagents is presented. The use of a commercially available nickel N-heterocyclic carbene (NHC) complex allows the reaction with a variety of (hetero)aryllithium compounds, including those prepared via metal-halogen exchange or direct metallation, whereas a commercially available electron-rich nickel-bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product. These reactions proceed rapidly (1h) under mild conditions (room temperature) while avoiding the undesired formation of reduced or homocoupled products.