Redox-neutral carbon–heteroatom bond formation under photoredox catalysis

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7004 - 7027

Published: Jan. 1, 2023

This feature article presents all the recent reports on photoredox-catalyzed redox-neutral carbon–heteroatom coupling reactions up to March 2023.

Language: Английский

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eFluorination Using Cheap and Readily Available Tetrafluoroborate Salts

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1353 - 1358

Published: March 1, 2023

A practical electrochemical method for the rapid, safer, and mild synthesis of tertiary hindered alkyl fluorides from carboxylic acids has been developed without need hydrofluoric acid salts or non-glass reactors. In this anodic fluorination, collidinium tetrafluoroborate acts as both supporting electrolyte fluoride donor. wide range functional groups shown to be compatible, possibility scale-up using flow electrochemistry also demonstrated.

Language: Английский

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Decarboxylative Sulfonylation of Carboxylic Acids under Mild Photomediated Iron Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2381 - 2386

Published: March 15, 2024

Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.

Language: Английский

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Selective Electrochemical Modification and Degradation of Polymers

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)

Published: Feb. 28, 2024

Abstract We demonstrate that electrochemical‐induced decarboxylation enables reliable post‐polymerization modification and degradation of polymers. Polymers containing N ‐(acryloxy)phthalimides were subjected to electrochemical under mild conditions, which led the formation transient alkyl radicals. By installing these redox‐active units, we systematically modified pendent groups chain ends polyacrylates. This approach enabled production poly(ethylene‐ co ‐methyl acrylate) poly(propylene‐ copolymers, are difficult synthesize by direct polymerization. Spectroscopic chromatographic techniques reveal transformations near‐quantitative on several polymer systems. Electrochemical also all‐methacrylate poly( ‐(methacryloxy)phthalimide‐ methacrylate) copolymers with a efficiency >95 %. Chain cleavage is achieved through ‐hydroxyphthalimide ester subsequent β‐scission backbone radical. Electrochemistry thus shown be powerful tool in selective controlled macromolecular degradation.

Language: Английский

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Unlocking carbene reactivity by metallaphotoredox α-elimination

Nature, Journal Year: 2024, Volume and Issue: 631(8022), P. 789 - 795

Published: June 6, 2024

Language: Английский

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