Issue 8, 2021

Merging radical-polar crossover/cycloisomerization processes: access to polyfunctional furans enabled by metallaphotoredox catalysis

Abstract

With the radical derived from alkyl silicates or 4-alkyl-1,4-dihydropyridines as the surrogate for the nucleophile, the cyclisation of 2-(1-alkynyl)-2-alken-1-ones proceeds smoothly via consecutive reductive radical-polar crossover and cycloisomerization processes enabled by dual photoredox–copper catalysis. Both single-electron oxidation and reduction occur between the photocatalyst and radical precursor/adduct radical, generating the enolate ion without the need for a base and an exogenous oxidant–reductant. In contrast to the reported transition-metal catalysed cyclisation with the oxonium ion as the key intermediate, the nucleophilic attack of enolate-oxygen on the copper coordinated alkyne was proposed for this dual catalysis. This new methodology for the preparation of polyfunctional furans features mild conditions, a broad substrate scope, and good functional group tolerance.

Graphical abstract: Merging radical-polar crossover/cycloisomerization processes: access to polyfunctional furans enabled by metallaphotoredox catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
25 Nov 2020
Accepted
01 Feb 2021
First published
01 Feb 2021

Org. Chem. Front., 2021,8, 1732-1738

Merging radical-polar crossover/cycloisomerization processes: access to polyfunctional furans enabled by metallaphotoredox catalysis

Y. Liu, W. Luo, T. Xia, Y. Fang, C. Du, X. Jin, Y. Li, L. Zhang, W. Lei and H. Wu, Org. Chem. Front., 2021, 8, 1732 DOI: 10.1039/D0QO01472A

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