Palladium-catalyzed Suzuki cross-coupling reactions in a microemulsion

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1445-1449

  Vashchenko, Valery ^a   Krivoshey, Alexander ^a   Knyazeva, Irina ^a   Petrenko, Alexey ^b   Goodby, John W ^c  

^a INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

^b UNIVERSITY OF HULL   (United Kingdom)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Cross coupling; Microemulsion; Palladium; Suzuki reaction

Indexed keywords

ALKYL GROUP; DODECYL SULFATE SODIUM; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; MICROEMULSION; QUANTITATIVE ANALYSIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY; SUZUKI REACTION; THERMOSTABILITY;

EID: 38749137341     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.013     Document Type: Article

References (28)

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7. Similar methodology was used recently for the case of bicyclic aziridines:. Zbruyev A.I., Vashchenko V.V., Andryushchenko A.A., Desenko S.M., Musatov V.I., Knyazeva I.V., and Chebanov V.A. Tetrahedron 63 (2007) 4297-4303
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27. 2(dppf) (44 mg, 0.06 mmol, 0.03 equiv) was added under argon and the degassing was repeated. The resultant emulsion was heated to reflux with stirring, and the areneboronic acid (2.4 mmol, 1.2 equiv) in n-butyl alcohol (0.7 ml) and toluene (2.5 ml) was added dropwise over 5-10 min. The reaction mixture was stirred at reflux until HPLC revealed that the reaction was complete. The reaction was then allowed to cool. The organic layer was separated, the water layer was extracted with toluene, the extracts were collected, washed with water and dried. In the case of base-insensitive materials, the reaction mixture was cooled, diluted with isopropyl alcohol (100 ml), evaporated to dryness and suspended in dichloromethane (25 ml). The resultant suspension was filtered through a short pad of silica, washed with dichloromethane (30 ml) and evaporated to dryness. The product obtained was purified by crystallization from an appropriate solvent.
28. 19), 1.6 mmol, 0.8 equiv). The reaction mixture was bubbled with argon while the bromide was added through a rubber septum via a syringe. The reaction mixture was then degassed and heated to reflux with stirring. A solution of sodium carbonate decahydrate (1.7 g, 6 mmol, 3 equiv) in water (3 ml) was thoroughly degassed by bubbling with argon and added quickly through the rubber septum into the reaction mixture via a syringe. A sample of the reactants was taken after a period of time measured from the addition of the base (Table 2).