Room Temperature Palladium-Catalyzed Cross Coupling of Aryltrimethylammonium Triflates with Aryl Grignard Reagents

Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functiona...

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Bibliographic Details
Published in:Organic letters 2010-10, Vol.12 (19), p.4388-4391
Main Authors: Reeves, Jonathan T, Fandrick, Daniel R, Tan, Zhulin, Song, Jinhua J, Lee, Heewon, Yee, Nathan K, Senanayake, Chris H
Format: Article
Language:English
Subjects:
Catalysis
Mesylates - chemical synthesis
Molecular Structure
Palladium - chemistry
Quaternary Ammonium Compounds - chemistry
Temperature
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Summary:Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated. Competition experiments established the reactivity of PhNMe3OTf relative to PhCl, PhBr, PhI, and PhOTf.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1018739