Highly Regioselective Catalytic Oxidative Coupling Reactions:  Synthetic and Mechanistic Investigations

Highly Regioselective Catalytic Oxidative Coupling Reactions:  Synthetic and Mechanistic Investigations

A highly efficient and regioselective Pd-catalyzed method for the oxidative coupling of arylpyridine derivatives is reported. Remarkably, the reactions proceed at room temperature and are compatible with diverse functionalities, including aryl halides and thiophenes. Mechanistic studies suggest that...

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Veröffentlicht in:Journal of the American Chemical Society 2006-11, Vol.128 (43), p.14047-14049
Hauptverfasser: Hull, Kami L, Lanni, Erica L, Sanford, Melanie S
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemistry
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Organic chemistry
Oxidation-Reduction
Reactivity and mechanisms
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Zusammenfassung:A highly efficient and regioselective Pd-catalyzed method for the oxidative coupling of arylpyridine derivatives is reported. Remarkably, the reactions proceed at room temperature and are compatible with diverse functionalities, including aryl halides and thiophenes. Mechanistic studies suggest that these transformations proceed via a previously unprecedented mechanism involving two different pyridine-directed C−H activation reactionsone at a PdII center and one at PdIV.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja065718e