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Synthesis of a versatile 1H-indene-3-carboxylate scaffold enabled by visible-light promoted Wolff rearrangement of 1-diazonaphthalen-2(1H)-ones. 2023
Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University, Changzhou, 21364, China. wgguo@cczu.edu.cn.
Herein, we have developed a sequential visible-light-promoted Wolff rearrangement of 1-diazonaphthalen-2(1H)-ones, followed by capturing the in situ generated ketene intermediates with various alcohols, producing diverse 1H-indene-3-carboxylates in moderate to good yields under mild reaction conditions. The broad substrate scope, high functional group tolerance, and robust conditions make the resulting derivative a versatile platform for the synthesis of plenty of bioactive molecules.
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