A Synthetic Approach to Dimetalated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions
A Synthetic Approach to Dimetalated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions
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DOI：
10.1021/jacs.0c06370
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发表时间：
2020-10-07
影响因子：
15
通讯作者：
Nagaki, Aiichiro
中科院分区：
文献类型：
--
作者：
Ashikari, Yosuke;Kawaguchi, Tomoko;Nagaki, Aiichiro
尽管它们具有潜在的用途，但二金属化芳烃的化学仍然处于起步阶段，因为它们非常难以合成。我们报道了一种新的方法，合成芳烃轴承硼基基团和金属取代基，如硼基，甲硅烷基，甲锡烷基，或锌基基团，在一个集成的流动微反应器的基础上产生和反应的芳基锂轴承三烷基硼酸酯部分。这些芳烃在钯催化的交叉偶联反应中表现出显著的化学选择性。通过选择构成二金属化芳烃的金属物质以及合适的催化剂来切换选择性。
In spite of their potential utility, the chemistry of dimetalated arenes is still in its infancy because they are extremely difficult to synthesize. We report a novel method of synthesizing arenes bearing a boryl group and a metallic substituent, such as boryl, silyl, stannyl, or zincyl groups, in an integrated flow microreactor based on the generation and reactions of aryllithiums bearing a trialkyl borate moiety. The bimetallic arenes showed a remarkable chemoselectivity in palladium-catalyzed cross-coupling reactions. The selectivity was switched by the selection of the metal species that constitutes the dimetalated arenes as well as appropriate catalysts.