A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups.
A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups.
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DOI：
10.1002/chem.201000876
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发表时间：
2010-09
期刊：
影响因子：
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通讯作者：
A. Nagaki;Heejin Kim;Yuya Moriwaki;Chika Matsuo;J. Yoshida
中科院分区：
文献类型：
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作者：
A. Nagaki;Heejin Kim;Yuya Moriwaki;Chika Matsuo;J. Yoshida
由微混合器和微管反应器组成的流动微反应器系统为在对位、间位和邻位带有烷氧基羰基的芳基锂的生成和反应提供了有效的工具。对硫代苯甲酸烷基酯和间硫代苯甲酸锂烷基酯通过与 PhLi 的 I/Li 交换反应生成。 Br/Li 与 sBuLi 的交换反应不成功。随后所得芳基锂与亲电子试剂的反应以良好的收率得到所需的产物。另一方面，通过与sBuLi的Br/Li交换反应成功生成了邻硫代苯甲酸烷基酯。随后与亲电子试剂的反应以良好的收率得到了所需的产物。
A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para-, meta-, and ortho-positions. Alkyl p- and m-lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o-lithiobenzoates were successfully generated by the Br/Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.