Stille reaction over cis-halocyclohexadienediol derivatives

Tetrahedron Letters

Volumn 49, Issue 48, 2008, Pages 6787-6790

  Heguaburu, Viviana ^a   Sá, Marcus Mandolesi ^b   Schapiro, Valeria ^a   Pandolfi, Enrique ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

cis Cyclohexadienediols; Microwave; Stille reaction

Indexed keywords

ALICYCLIC HYDROCARBON; BENZENE DERIVATIVE; BUTYLTIN DERIVATIVE; HYDROXYL GROUP; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HEATING; MICROWAVE IRRADIATION; STILLE REACTION;

EID: 53749103563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.049     Document Type: Article

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25. 5 Microwave reactions were performed in a commercially available monomode reactor (CEM Explorer). Reactions were carried out in 10 mL Pyrex vials sealed with septa and using magnetic stirring. General procedure for Stille reaction using microwave heating: To a solution of cis-dihydrodiol derivative (0.37 mmol) and tetrakis(triphenylphosphine) palladium (0) (63 mg, 0.055 mmol) in anhydrous THF (2 mL), allyltributyltin was added (0.12 mL, 0.40 mmol). The mixture was irradiated in a microwave at 90-120 °C and 200 W for 5-10 min in a sealed tube under a nitrogen atmosphere. Removal of the solvent and purification by flash chromatography on silica gel (EtOAc/hexanes) gave the cross-coupling product.
26. 2 = 7.7 Hz, 1H), 2.90 (m, 1H), 2.74 (d, J = 7.1 Hz, 1H), 2.55 (d, J = 4.4 Hz, 1H), 1.43 (s, 3H), 1.36 (s, 3H) ppm.