Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates

Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates

We previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to exc...

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Veröffentlicht in:Journal of organic chemistry 2008-03, Vol.73 (6), p.2052-2057
Hauptverfasser: Molander, Gary A, Gormisky, Paul E, Sandrock, Deidre L
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemical synthesis
Amines - chemistry
Benzene Derivatives - chemical synthesis
Benzene Derivatives - chemistry
Borates - chemistry
Catalysis
Chemistry
Chlorobenzenes
Exact sciences and technology
Hydrocarbons, Halogenated - chemistry
Methylation
Noncondensed benzenic compounds
Organic chemistry
Palladium
Preparations and properties
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Zusammenfassung:We previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800183q