A mild and efficient carboxylate-directed C–H arylation of aryl carboxylic acids with iodobenzenes in water

Xu, Zhongmiao; Yang, Ting; Lin, Xichen; Elliott, John D.; Ren, Feng

doi:10.1016/j.tetlet.2014.12.001

Cited by 27 publications

(13 citation statements)

References 20 publications

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“…Ren ( Scheme 7B ) reported a selective mono-arylation with aryl iodides in water (with the use of TWEEN 20 as a surfactant). 114 The yields were generally good to excellent. However, some sensitivity to steric hindrance in ortho substituted benzoic acids was observed.…”

Section: Carboxylic Acids As Dgmentioning

confidence: 94%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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Section: Carboxylic Acids As Dgmentioning

confidence: 94%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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“…Use of the polysorbate Tween 20 (see Scheme ) enables Pd‐catalyzed ortho ‐arylation of aromatic carboxylic acids in water at 80 °C . Aryl iodides are the coupling partners, with silver trifluoroacetate found to be essential to remove iodide ion from the reaction mixture.…”

Section: Spotlight On Pd Catalysismentioning

confidence: 99%

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

Lipshutz

Ghorai²,

Cortes‐Clerget

2018

Chemistry A European J

305

182

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Recent developments over the past few years in aqueous micellar catalysis are discussed. Applications to problems in synthesis are highlighted, enabled by the use of surfactants that self-aggregate in water into micelles as nanoreactors. These include amphiphiles that have been available for some time, as well as those that have been newly designed. Reactions catalyzed by transition metals, including Pd, Cu, Rh, and Au, are of particular focus.

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“…Several research groups have independently reported the palladium-catalyzed ortho -C–H bond arylation of carboxylic acids. 16 We thus combined the ortho -C–H arylation protocol of carboxylic acid with the sequential fluorination 17 and the present decarbonylative C–F bond alkylation (Scheme 4). As the first step, we synthesized 3-aryl-2-naphthoic acids ( 6a – d ) in 45–62% yields under modified conditions of Daugulis’ procedure.…”

Section: Resultsmentioning

confidence: 99%

Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Fluorides Assisted by Lewis-Acidic Organoboranes

Okuda

Ishida

et al. 2018

ACS Omega

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Herein, nickel-catalyzed decarbonylative C–F bond alkylation of aroyl fluorides with organoboron reagents is reported. Aroyl fluorides are more chemically stable than the corresponding aroyl chlorides and can be readily synthesized from the corresponding carboxylic acids. The fluoronickel intermediate formed via oxidative addition interacts with Lewis-acidic trialkylboranes, and the subsequent decarbonylative alkylation proceeds. This new synthetic methodology allows 1,2-bifunctionalization of aromatic carboxylic acids via palladium-catalyzed ortho -C–H arylation. In addition, an unprecedented 1,4-nickel migration on ortho -arylated aroyl fluorides was observed. As a demonstration of the synthetic utility of the present reaction, the sequential 1-alkyl-2-arylation of 3-hydroxy-2-naphthoic acid was accomplished via chemoselective alkylation at a fluorocarbonyl moiety and the subsequent C–O bond arylation at an acetoxy group.

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A mild and efficient carboxylate-directed C–H arylation of aryl carboxylic acids with iodobenzenes in water

Cited by 27 publications

References 20 publications

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Fluorides Assisted by Lewis-Acidic Organoboranes

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