Wu Yinsong, He Xinwei, Xie Mengqing, Li Ruxue, Ning Yi, Duan Jiahui, Zhang Enshen, Shang Yongjia
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. China.
J Org Chem. 2021 Jun 4;86(11):7370-7380. doi: 10.1021/acs.joc.1c00259. Epub 2021 May 20.
A Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds (e.g., 1,3-diketones and β-keto esters) is achieved to afford 6,7-dihydrobenzofuran-4(5)-ones in up to 91% yields. Notably, a wide range of substrates and functional groups were well-tolerated under the optimized reaction conditions to give desired products in moderate to excellent yields with release of N and HO as byproducts. Moreover, the method described is scalable and adaptable to late-stage functionalization.
实现了铑（III）催化的2-重氮-1,3-二酮与1,3-二羰基化合物（如1,3-二酮和β-酮酯）的级联亲核加成/分子内环化反应，以高达91%的产率得到6,7-二氢苯并呋喃-4（5）-酮。值得注意的是，在优化的反应条件下，各种底物和官能团都能很好地耐受，以中等至优异的产率得到所需产物，并释放出N₂和H₂O作为副产物。此外，所描述的方法具有可扩展性，适用于后期官能团化。
