6533b82cfe1ef96bd128f61d
RESEARCH PRODUCT
Deprotonation of Thiophenes Using Lithium Magnesates.
Christophe HoarauOmar BayhHaçan AwadBelén AbarcaRafael BallesterosFrancis MarsaisFrançois TrécourtFlorence MonginGuy QuéguinerFernando Blancosubject
ArylOrganic Chemistrychemistry.chemical_elementGeneral MedicinePhotochemistryBiochemistryMedicinal chemistryCatalysischemistry.chemical_compoundDeprotonationchemistryDrug DiscoveryElectrophileThiopheneReactivity (chemistry)LithiumPalladiumdescription
Abstract Thiophene was regioselectively deprotonated at C2 on treatment with 1/3 equiv of Bu3MgLi in THF at room temperature. The lithium arylmagnesate formed was either trapped with electrophiles or cross-coupled in a ‘one-pot’ procedure with aryl halides under palladium catalysis. 2-Chlorothiophene and 2-methoxythiophene were similarly deprotonated at C5 under the same reaction conditions. The enhancement of the reactivity of the base using TMEDA was evidenced using 1H NMR spectroscopy.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-08-30 | ChemInform |