Blue Vitriol Catalyzed Decarboxylative C–C Cross-Coupling of α,β-Unsaturated Acids for C–H Functionalization of Unactivated Ethers

Herein, we introduce a visible-light-induced copper-catalyzed decarboxylative C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-coupling of α,β-unsaturated carboxylic acids with unactivated cyclic ethers. The protocol employs an underexplored catalytic combination of CuSO<sub>4</sub>·5H<sub>2</sub>O/sodium L-(+)-ascorbate merged with an iridium photocatalyst for enabling direct C2-selective functionalization of cyclic ethers under ambient conditions. This transformation provides modular access to 2-oxyalkylated ketones via a rare anti-Giese-type radical addition. A wide range of cinnamic acid derivatives, including electron-rich, electron-deficient, heteroaryl, and sterically hindered substrates, as well as complex bioactive and natural product-derived motifs, have been tolerated with excellent yields. Detailed mechanistic investigations support a Cu/Ir dual-catalytic pathway involving oxygen-derived radical intermediates and copper-assisted decarboxylation.

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Publication Details

Journal
Organic Letters
Published
2026-03-26
DOI
https://doi.org/10.1021/acs.orglett.6c00723
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Blue Vitriol Catalyzed Decarboxylative C–C Cross-Coupling of α,β-Unsaturated Acids for C–H Functionalization of Unactivated Ethers

Souvik Maiti, Subal Mondal, Pradyut Ghosh, Siba P. Midya et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Blue Vitriol Catalyzed Decarboxylative C–C Cross-Coupling of α,β-Unsaturated Acids for C–H Functionalization of Unactivated Ethers

Souvik Maiti, Subal Mondal, Pradyut Ghosh, Siba P. Midya, Soumya Mondal
article en

Abstract

Herein, we introduce a visible-light-induced copper-catalyzed decarboxylative C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-coupling of α,β-unsaturated carboxylic acids with unactivated cyclic ethers. The protocol employs an underexplored catalytic combination of CuSO<sub>4</sub>·5H<sub>2</sub>O/sodium L-(+)-ascorbate merged with an iridium photocatalyst for enabling direct C2-selective functionalization of cyclic ethers under ambient conditions. This transformation provides modular access to 2-oxyalkylated ketones via a rare anti-Giese-type radical addition. A wide range of cinnamic acid derivatives, including electron-rich, electron-deficient, heteroaryl, and sterically hindered substrates, as well as complex bioactive and natural product-derived motifs, have been tolerated with excellent yields. Detailed mechanistic investigations support a Cu/Ir dual-catalytic pathway involving oxygen-derived radical intermediates and copper-assisted decarboxylation.

Organic Letters
Indian Association for the Cultivation of Science (IN)
Openalex Percentile: Top 5%
Catalytic C–H Functionalization Methods
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