Microwave-promoted Suzuki-Miyaura coupling reactions in a cycloalkane-based thermomorphic biphasic system

Tetrahedron Letters

Volumn 47, Issue 2, 2006, Pages 171-174

  Hayashi, Kanako ^a   Kim, Shokaku ^a   Kono, Yusuke ^a   Tamura, Mihoko ^a   Chiba, Kazuhiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Cycloalkane; Microwave; Suzuki Miyaura cross coupling; Thermomorphic

Indexed keywords

CYCLOALKANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COOLING; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; RACEMIC MIXTURE; SUZUKI REACTION;

EID: 28644443614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.161     Document Type: Article

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34. More than 99% of product (3a-j) was partitioned in the upper cycloalkane phase.
35. 1H NMR (less than 0.05 mol %).
36. 4 (32 mg, 0.15 mmol) and phenylboronic acid (0.1 mmol) in 0.4 ml of DMF was treated with aryl halides attached to the cycloalkane-soluble platform (55 mg, 0.05 mmol) dissolved in 3.6 ml of methylcyclohexane. The solution was degassed under Ar and irradiated a microwave (microwave power was 150 W, 110°C, 5 min). After cooling, methylcyclohexane layer was separated and evaporated under vacuum. Methanol was added to the residue followed by filtration to afford the biaryl product 3a-j. This reaction was achieved in up to 0.1 M scale to give the products in almost the same yields as the above condition.