Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands

Organic Letters

Volumn 11, Issue 2, 2009, Pages 381-384

  Yang, David X ^a   Colletti, Steven L ^a   Wu, Kevin ^b   Song, Maoying ^b   Li, George Y ^b   Shen, Hong C ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b CombiPhos Catalysts Inc ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; ESTER; HALOGEN; LIGAND; OXIDE; PALLADIUM; PHOSPHINE; PHOSPHINE DERIVATIVE;

AIR; ARTICLE; CATALYSIS; CHEMISTRY;

AIR; BORONIC ACIDS; CATALYSIS; ESTERS; HALOGENS; LIGANDS; OXIDES; PALLADIUM; PHOSPHINES;

EID: 61449215236     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802642g     Document Type: Article

References (23)

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22. General Procedure. To a sealed tube were added aryl bromide (1 equiv), boronic ester (1.2 equiv), base (2 equiv), solvent, and catalyst (3 mol %). The sealed tube was then heated at 90 °C over 18 h. After 1 h, to the mixture were added dichloromethane and water. The organic layer was concentrated and purified by silica gel chromatography eluting with ethyl acetate and hexanes to give the desired product.
23. In ref 5, Buchwald and Billinsley utilized lithium triisopropyl 2-pyridylborates. Presumably similar lithium borate species were formed in situ here from boronic esters and lithium alkoxides.