Synthesis of cyclopenta[b]benzofurans via biomimetic oxidative phenol–enamine [3 + 2] cycloaddition?
Organic Chemistry Frontiers Pub Date: 2023-01-14 DOI: 10.1039/D2QO01916G
Abstract
A hemin/t-BuOOH-catalyzed oxidative phenol–enamine formal [3 + 2] cycloaddition has been developed, enabling the environmentally benign synthesis of valuable cyclopenta[b]benzofuran scaffolds under sustainable reaction conditions with excellent atom- and step-economy. Mechanistic studies point to the involvement of a two-electron oxidation pathway. Based on the preliminary biological investigations, compound 3ay displayed moderate anti-cancer activities (IC50 = 27.73 μM) against MCF7 cells (breast cancer cells).
![Graphical abstract: Synthesis of cyclopenta[b]benzofurans via biomimetic oxidative phenol–enamine [3 + 2] cycloaddition](http://scimg.chem960.com/usr/1/D2QO01916G.jpg)
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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