What question did this study set out to answer?

To establish an efficient palladium-catalyzed carbonylative cross-coupling protocol between arylboronic acids and aryl electrophiles for the synthesis of unsymmetrical biaryl and aryl benzyl ketones.

June 23, 1998The Journal of Organic Chemistry

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

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Authors

TITatsuo IshiyamaHokkaido University HKHiroe KizakiHokkaido University THTakahiro HayashiKurashiki Central Hospital

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Implication

Experimental study demonstrates selective synthesis of biaryl ketones via palladium-catalyzed carbonylative cross-coupling under atmospheric carbon monoxide, highlighting versatile synthetic utility.

Key Points

To establish an efficient palladium-catalyzed carbonylative cross-coupling protocol between arylboronic acids and aryl electrophiles for the synthesis of unsymmetrical biaryl and aryl benzyl ketones.
Conducted reactions in anisole at 80 °C under an atmospheric pressure of carbon monoxide in the presence of potassium carbonate base.
Employed 3 mol % PdCl2(PPh3)2 for aryl iodides, and 3 mol % PdCl2(dppf) combined with 3 equivalents of potassium iodide for aryl bromides and triflates.
Applied the carbonylative cross-coupling strategy to benzyl halides to generate aryl benzyl ketones.
Carbonylative cross-coupling selectively produced unsymmetrical biaryl ketones under mild atmospheric pressure of carbon monoxide.
Addition of potassium iodide enabled the coupling of typically less reactive aryl bromides and aryl triflates using the PdCl2(dppf) catalytic system.
Substrate scope extended to benzyl halides, facilitating the synthesis of aryl benzyl ketones.

Cite This Study

Ishiyama et al. (1998) studied this question.

synapsesocial.com/papers/6a6f2e756c240de38cdb696b https://doi.org/10.1021/jo980417b

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Implication

Experimental study demonstrates selective synthesis of biaryl ketones via palladium-catalyzed carbonylative cross-coupling under atmospheric carbon monoxide, highlighting versatile synthetic utility.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Discussion

Member takes

Implication

Key Points

Cite This Study

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Discussion

Member takes

Implication

Key Points

Cite This Study

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