Department of Chemistry, University of Chicago, Chicago, IL 60637, USA.
Angew Chem Int Ed Engl. 2018 Feb 5;57(6):1697-1701. doi: 10.1002/anie.201712393. Epub 2018 Jan 16.
Herein we report a direct annulation between aryl iodides and epoxides through palladium/norbornene (Pd/NBE) cooperative catalysis. An iso-propyl ester substituted NBE was found to be most efficient to suppress the formation of multiple-NBE-insertion byproducts and affords the desired 2,3-dihydrobenzofuran derivatives in 44-99 % yields. The reaction is scalable and tolerates a range of functional groups. Asymmetric synthesis is realized using an enantiopure epoxide. Application of this method into a concise synthesis of insecticide fufenozide is demonstrated.
在此,我们报告了通过钯/降冰片烯(Pd/NBE)协同催化,芳基碘化物和环氧化物之间的直接环化反应。发现异丙酯取代的 NBE 最有效地抑制了多-NBE-插入副产物的形成,并以 44-99%的收率得到了所需的 2,3-二氢苯并呋喃衍生物。该反应可规模化进行,并可耐受多种官能团。使用手性环氧丙烷实现了不对称合成。该方法在杀虫剂虱螨脲的简洁合成中的应用得到了证明。