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DOI: 10.1055/s-0028-1087368
Propylene Oxide Assisted Sonogashira Coupling Reaction
Publikationsverlauf
Publikationsdatum:
26. November 2008 (online)
Abstract
A propylene oxide assisted base-free Sonogashira cross-coupling reaction has been developed. The unique feature of the current protocol has extended the scope of Sonogashira reaction to some base-sensitive substrates.
Key words
base-free - propylene oxide - Sonogashira reaction
- Supporting Information for this article is available online:
- Supporting Information
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General Procedure: The Batey Pd-carbene complex 1 (2.5 mol%), CuI (5 mol%), Ph3P (2.5 mol%) and DMF (2 mL) were added to a dry 10-mL septum-capped round-bottomed flask under a nitrogen atmosphere. Aryl iodide (2 mmol), alkyne (110 mol%), and PO (5 equiv) were then added to the above mixture. While the mixture was stirred, the flask was cooled to -78 ˚C, vacuumed, and charged with nitrogen. This process was repeated for three times. After the mixture was warmed to 25 ˚C, stirring was continued at that temperature for 48 h. The mixture was diluted with H2O and extracted with E2O. The organic extracts were combined, washed with brine, dried (MgSO4), filtered, and concentrated to give a residue, which was purified by flash column chromatography on silica gel.
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