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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation
Barbora Lemrová1, Michal Maloň2, Miroslav Soural1,3
1Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 12, 77146 Olomouc, Czech Republic. Miroslav.Soural@upol.cz.
Abstract:
Immobilized L-aspartic acid beta-methyl ester (Fmoc-Asp(OMe)-OH) was reacted with 4-nitrobenzenesulfonyl chloride, followed by alkylation with various α-haloketones. The resulting intermediates were treated with potassium trimethylsilanolate, which yielded tetrasubstituted pyrroles after a one-step transformation consisting of sequential C-arylation, aldol condensation and spontaneous aromatization. The discovered synthetic strategy enables fast and simple access to pentasubstituted and functionalized pyrroles from a number of readily available starting materials.
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