Weidmann Niels, Harenberg Johannes H, Knochel Paul
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 München, Germany.
Org Lett. 2020 Aug 7;22(15):5895-5899. doi: 10.1021/acs.orglett.0c01991. Epub 2020 Jul 23.
Herein we report the generation of benzylic lithiums via an iodine-lithium exchange reaction on benzylic iodides performed in continuous flow using BuLi as the exchange reagent. The resulting benzylic lithium species are trapped in situ by carbonyl electrophiles under Barbier conditions, resulting in benzylic secondary and tertiary alcohols. This flow procedure further allows the generation of highly reactive heterobenzylic lithium compounds, which are difficult to generate under batch conditions. A general scale-up was possible without further optimization.
在此，我们报道了通过在连续流动条件下使用丁基锂作为交换试剂，对苄基碘进行碘-锂交换反应来生成苄基锂。所得的苄基锂物种在巴比耶条件下被羰基亲电试剂原位捕获，生成苄基仲醇和叔醇。这种流动方法还能生成在间歇条件下难以生成的高活性杂苄基锂化合物。无需进一步优化即可实现普遍的放大反应。
