Brønsted Acid-Catalyzed Tandem Double Friedel–Crafts Alkylation to Construct a Dihydrophenalene Skeleton Bearing an All-Carbon Quaternary Center
Authors:
- 25 December 2023
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 89 (1) , 576-588
Abstract
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.Keywords
Funding Information
- National Natural Science Foundation of China (U21A20287)
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