Copper-Catalyzed Coupling of Arylboronic Acids and Amines

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2077-2079

  Antilla, Jon C ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORONIC ACID DERIVATIVE; COPPER; TOLYLBORONIC ACID;

ARTICLE; CATALYSIS; CHEMISTRY; TEMPERATURE;

AMINES; BORONIC ACIDS; CATALYSIS; COPPER; TEMPERATURE;

EID: 0035963683     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0160396     Document Type: Article

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26. 2 (5-20 mol %), and myristic acid (10-40 mol %) were combined in a 100-mL round-bottom flask with a large stir bar. A rubber septum was attached, and dry toluene (2 mL), 2.6-lutidine (1.0 mmol). and the amine (1.0 mmol) were successively added by syringe. The resulting mixture was stirred at a high rate for 24 h, diluted with ethyl acetate (10 mL), filtered through a plug of silica gel, and then purified by column chromatography to give the desired product (see Supporting Information).
27. Brief attempts to arylate imidazoles with this method resulted in low yields (32%) of the desired product.