布朗斯特酸催化串联双傅克烷基化反应构建含全碳季碳中心的二氢菲骨架。
Brønsted Acid-Catalyzed Tandem Double Friedel-Crafts Alkylation to Construct a Dihydrophenalene Skeleton Bearing an All-Carbon Quaternary Center.
作者信息
OuYang Mingjing, Yuan Min, Li Jinwei, Yang Wen
机构信息
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.
出版信息
J Org Chem. 2024 Jan 5;89(1):576-588. doi: 10.1021/acs.joc.3c02310. Epub 2023 Dec 25.
An efficient Brønsted acid-catalyzed tandem reaction has been developed for the construction of a dihydrophenalene skeleton bearing an all-carbon quaternary center. Starting with 2-naphthol-tethered ketones and indoles, the tandem reaction catalyzed by TsOH monohydrate proceeded smoothly with good to excellent efficiency through a double Friedel-Crafts alkylation process. Moreover, the synthetic utility of this method was demonstrated by easy gram-scale preparation and product transformations to fused hexacyclic compounds.
已开发出一种高效的布朗斯特酸催化串联反应，用于构建带有全碳季中心的二氢菲骨架。以2-萘酚连接的酮和吲哚为起始原料，一水合对甲苯磺酸催化的串联反应通过双傅克烷基化过程顺利进行，效率良好至优异。此外，该方法的合成实用性通过简便的克级制备以及产物转化为稠合六环化合物得到了证明。
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