Synthesis of Highly Functionalized Diaryl Ketones by Palladium‐Catalyzed Carbonylative Cross‐Coupling Reaction Between Triarylbismuthines and Aryl(Heteroaryl) Iodides

Highly functionalized diaryl ketones were prepared by carbonylative cross‐coupling reaction between triarylbismuthines and aryl and heteroaryl iodides. The reaction is catalyzed by tetrakis(triphenylphosphine)palladium(0) and is performed in the presence of rubidium carbonate. The procedure requires...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2017-03, Vol.2 (8), p.2593-2599
Main Authors: Dansereau, Julien, Gautreau, Stéphane, Gagnon, Alexandre
Format: Article
Language:English
Subjects:
Carbonylation
Cross-coupling reaction
Diaryl ketones
Palladium catalysis
Triarylbismuthines
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Summary:Highly functionalized diaryl ketones were prepared by carbonylative cross‐coupling reaction between triarylbismuthines and aryl and heteroaryl iodides. The reaction is catalyzed by tetrakis(triphenylphosphine)palladium(0) and is performed in the presence of rubidium carbonate. The procedure requires only 1 atmosphere of carbon monoxide and 0.4 equivalents of triarylbismuthine. Addition of lithium chloride provides higher yields of the desired diaryl ketones. This simple protocol shows wide substrate scope and excellent functional group tolerance. The reactivity of ditolylbismuth chloride and tolylbismuth dichloride is investigated. A simple and efficient method has been developed for the carbonylative cross‐coupling reaction of triarylbismuthines with aryl(heteroaryl) iodides. The reaction is catalyzed by commercially available tetrakis(triphenylphosphine)palladium(0) and is performed under 1 atmosphere of carbon monoxide. The use of lithium chloride as an additive and rubidium carbonate as a base provides higher yields of the desired diarylketones. The protocol shows high functional group tolerance.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201700438