Tetrabutylammonium 2‑Pyridyltriolborate Salts for Suzuki–Miyaura Cross-Coupling Reactions with Aryl Chlorides

Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corre...

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Bibliographic Details
Published in:Organic letters 2013-09, Vol.15 (17), p.4308-4311
Main Authors: Sakashita, Shohei, Takizawa, Miho, Sugai, Juugaku, Ito, Hajime, Yamamoto, Yasunori
Format: Article
Language:English
Subjects:
Borates - chemical synthesis
Borates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Chlorinated - chemistry
Molecular Structure
Palladium - chemistry
Quaternary Ammonium Compounds - chemical synthesis
Quaternary Ammonium Compounds - chemistry
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Summary:Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH2CH2OH (20 mol %) in anhydrous DMF without bases.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402268g