Ligand-free palladium catalysis of aryl coupling reactions facilitated by grinding

Tetrahedron Letters

Volumn 44, Issue 4, 2003, Pages 765-768

  Klingensmith, Liane M ^a   Leadbeater, Nicholas E ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; LIGAND; PALLADIUM;

AIR; ARTICLE; CATALYSIS; CHEMICAL REACTION; GRINDING; MOISTURE; STOICHIOMETRY;

LATEOLABRAX JAPONICUS;

EID: 0037455093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02645-X     Document Type: Article

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36. Grinding experiments were performed using a Retsch® Mixer Mill Type MM 200 (http://www.retsch.de/index.php). Samples were loaded into 10 ml capacity screw cap stainless steel grinding jars. The vibration frequency of the mixer mill was set to 30 Hz (1800 rpm). Stirring experiments were performed in small test tubes which, after loading with the reagents, were sealed with a septum to prevent evaporation.
37. 1H NMR analysis using 1,2-dichloroethene as an internal standard. For isolation of products, in the cases where the starting aryl halide was a liquid unreacted aryl halide was firstly removed by heating the crude residue whilst under a vacuum on a Schlenk line. Products were purified by recrystallization, or flash chromatography on silica gel using hexane or hexane/ethyl acetate as eluent.
38. 3 (3 mmol, 510 mg) and triethylamine (300 mg, 0.41 ml, 3 mmol). NaCl was added slowly to the reaction mixture with agitation with a spatula until a damp paste was formed. The consistency of the paste was such that no liquid remained in the grinding jar but the granules of NaCl clung to the spatula when lifted from the mixture. A grinding ball was then added, the jar closed and placed into the mixer mill and the reaction mixture ground for 30 min. The grinding jar was then opened and the contents worked up in an identical manner to the Suzuki reactions.