Heck Heterocoupling within a Dendritic Nanoreactor

Nano Letters

Volumn 1, Issue 1, 2001, Pages 14-17

  Yeung, Lee K ^a   Crooks, Richard M ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002737158     PISSN: 15306984     EISSN: None     Source Type: Journal    
DOI: 10.1021/nl0001860     Document Type: Article

References (26)

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11. Fluorous/organic bi-phasic Heck reactions. A reaction flask containing the dried catalyst from above was charged with 3 mL of perfluoro-2-butyl-tetrahydrofuran (FC-75), 1.5 mL of heptane, and 1.5 mL of benzene. The mixture was degassed using three freeze-pump-thaw cycles. 0.63 mmol of aryl halide, 0.63-1.89 mmol of butylacrylate, and 0-1.89 mmol of triethylamine were added, depending on the desired stoichiometry (Table 1). The bi-phasic solvent mixture was then heated to 85°C, which formed a homogeneous reaction solution that was refluxed at 90°C for 24 h. The organic phase was separated from the fluorous phase by letting the reaction mixture cool slowly to room temperature. The organic layer was removed, and diethyl ether was added to the fluorous phase to ensure total extraction of the product. The organic phases were combined and washed with dilute HCl solution followed by deionized water. Upon removal of the solvent, the product (1) was isolated in 19-70% yield, and the purity was confirmed by NMR.
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