Herath Ananda, Molteni Valentina, Pan Shifeng, Loren Jon
Genomics Institute of the Novartis Research Foundation , 10675 John Jay Hopkins Drive , San Diego , California 92121 , United States.
Org Lett. 2018 Dec 7;20(23):7429-7432. doi: 10.1021/acs.orglett.8b03156. Epub 2018 Nov 14.
A versatile flow synthesis method for in situ formation of organozinc reagents and subsequent cross-coupling with aryl halides and activated carboxylic acids is reported. Formation of organozinc reagents is achieved by pumping organic halides, in the presence of ZnCl and LiCl, through an activated Mg-packed column under flow conditions. This method provides efficient in situ formation of aryl, primary, secondary, and tertiary alkyl organozinc reagents, which are subsequently telescoped downstream to a Negishi or decarboxylative Negishi cross-coupling reaction. The described method offers access to a variety of C-C bond formations with organozinc reagents that are otherwise commercially unavailable or difficult to prepare under traditional batch reaction conditions.
报道了一种通用的流动合成方法，用于原位形成有机锌试剂，并随后与芳基卤化物和活性羧酸进行交叉偶联。在流动条件下，通过将有机卤化物在ZnCl和LiCl存在下泵入装有活性Mg的柱中，实现有机锌试剂的形成。该方法能高效原位形成芳基、伯、仲和叔烷基有机锌试剂，随后在下游串联进行Negishi或脱羧Negishi交叉偶联反应。所描述的方法提供了利用有机锌试剂形成各种碳-碳键的途径，而这些有机锌试剂在传统间歇反应条件下要么无法商购，要么难以制备。
