Free Carboxylic Acids: The Trend of Radical Decarboxylative Functionalization

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(21)

Published: April 7, 2023

Abstract The exceptional versatility of carboxylic acids has been extensively exploited in organic synthesis across several decades. There a recent upsurge radical decarboxylative transformations. process can be initiated under mild conditions, and the resultant radicals have orthogonal reactivities to closed‐shell species, thus providing immense opportunities for streamlining novel reactions. use free is most desirable owing its high atom step economy. Aiming demonstrate attractiveness strategy inspire chemists tackle existing challenges, this review outlines advances on functionalization acids.

Language: Английский

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An iron-catalyzed C–S bond-forming reaction of carboxylic acids and hydrocarbons via photo-induced ligand to metal charge transfer

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4764 - 4773

Published: Jan. 1, 2023

A photo-induced iron-catalyzed strategy that facilitates the transformation of carboxylic acids and hydrocarbons into thioethers sulfoxides is herein reported.

Language: Английский

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The great strides of iron photosensitizers for contemporary organic photoredox catalysis: On our way to the holy grail?

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 500, P. 215522 - 215522

Published: Nov. 9, 2023

Language: Английский

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Radical-Mediated Decarboxylative C–C and C–S Couplings of Carboxylic Acids via Iron Photocatalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1110 - 1115

Published: Jan. 26, 2024

Despite the significant success of decarboxylative radical reactions, catalytic systems vary considerably upon different acceptors, requiring renewed case-by-case reaction optimization. Herein, we developed an iron condition that enables highly efficient decarboxylation various carboxylic acids for a range transformations. This operationally simple protocol was amenable to wide array delivering structurally diverse oxime ethers, alkenylation, alkynylation, thiolation, and amidation products in useful excellent yields (>40 examples, up 95% yield).

Language: Английский

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Visible-light induced direct C(sp³)–H functionalization: recent advances and future prospects

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

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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Unleashing the potentiality of metals: synergistic catalysis with light and electricity

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4024 - 4040

Published: Jan. 1, 2024

This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.

Language: Английский

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Iron-catalyzed fragmentation-alkynylation, -alkenylation and -alkylation cascade enabled by photoinduced ligand-to-metal charge transfer

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1729 - 1735

Published: Jan. 1, 2024

An iron-catalyzed fragmentation alkynylation, alkenylation and alkylation enabled by photoinduced ligand-to-metal charge transfer (LMCT)processis herein reported.

Language: Английский

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A survey of the iron ligand-to-metal charge transfer chemistry in water

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3058 - 3071

Published: Jan. 1, 2024

Fully hydrated! – Iron photocatalysis tests the waters.

Language: Английский

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Visible-Light-Induced Esterification of Carboxylic Acids with Arylsulfonium Salts

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 26, 2025

A photoinduced copper-mediated acyloxylation of arylthianthrenium or arylphenoxathiinium salts with either aliphatic aromatic carboxylic acids is described for the convenient synthesis O-aryl esters. The reaction has shown obvious advantages, such as high efficiency, good functional group tolerance, excellent chemoselectivity, and capacity esterification complex drug molecules, offering a practical synthetic route to multifunctionalized sterically congested esters, which are potentially useful in development new prodrugs twin drugs.

Language: Английский

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