Ruthenium-Catalyzed Cross-Coupling of Ketones as an Alkenyl Electrophile with Organoborons via Cleavage of Alkenyl C–N Bonds of in Situ Generated Enamines

A ruthenium-catalyzed cross-coupling reaction of ketones with organoboronic esters was developed. In this reaction, ketones possessing a pyridine-directing group directly functions as an alkenyl electrophile for coupling with organoboronates in the presence of pyrrolidine and a ruthenium catalyst. T...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (50), p.9233-9237
Main Authors: Kogure, Yuya, Ueno, Satoshi
Format: Article
Language:English
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Summary:A ruthenium-catalyzed cross-coupling reaction of ketones with organoboronic esters was developed. In this reaction, ketones possessing a pyridine-directing group directly functions as an alkenyl electrophile for coupling with organoboronates in the presence of pyrrolidine and a ruthenium catalyst. This reaction proceeds via the catalytic cleavage of the alkenyl carbon–nitrogen bond in the enamines generated in situ from ketones with pyrrolidine, benzylamine, or isoindoline.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03765