Mulryan Daniel, White Andrew J P, Crimmin Mark R
Department of Chemistry, Molecular Sciences Research Hub, Imperial College London, White City, Shepherds Bush, London W12 0BZ, United Kingdom.
Org Lett. 2020 Dec 4;22(23):9351-9355. doi: 10.1021/acs.orglett.0c03593. Epub 2020 Nov 17.
A new organocatalyzed fluoride metathesis reaction between fluoroarenes and carbonyl derivatives is reported. The reaction exchanges fluoride (F) and alternate nucleophiles (OAc, OCOR, SR, Cl, CN, NCS). The approach provides a conceptually novel route to manipulate the fluorine content of organic molecules. When the fluorination and defluorination steps are combined into a single catalytic cycle, a byproduct free and 100% atom-efficient reaction can be achieved.
报道了一种氟代芳烃与羰基衍生物之间新的有机催化氟交换反应。该反应可实现氟(F)与其他亲核试剂(乙酸根、酰氧基、硫烷基、氯、氰基、硫氰酸根)的交换。这种方法为控制有机分子中的氟含量提供了一种概念上全新的途径。当氟化和脱氟步骤合并到一个单一的催化循环中时,可实现无副产物且原子利用率为100%的反应。