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Article Dans Une Revue Tetrahedron Letters Année : 2012

Palladium-Catalysed Direct Arylations of NH-Free pyrrole and N-tosylpyrrole with Aryl Bromides

Résumé

The palladium-catalysed direct coupling of aryl halides with pyrroles provides a greener access to arylated pyrroles than more classical couplings such as Suzuki, Stille or Negishi reactions. However, so far, NH-free pyrrole and N-tosylpyrrole gave disappointing results for such couplings either in terms of regioselectivity of the arylation, catalyst loading or substrate scope. The reactivity of both NH-free pyrrole and N-tosylpyrrole was studied, and the tosylated pyrrole led to higher yields of coupling products due to better conversions of the aryl bromides. A range of aryl bromides undergo regioselective coupling at C2 of N-tosylpyrrole in moderate to good yields using 1 mol % [Pd(Cl(C3H5)]2 as the catalyst, KOAc as the base in DMAc.
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Dates et versions

hal-00868530 , version 1 (01-10-2013)

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Charles Beromeo Bheeter, Jitendra K. Bera, Henri Doucet. Palladium-Catalysed Direct Arylations of NH-Free pyrrole and N-tosylpyrrole with Aryl Bromides. Tetrahedron Letters, 2012, 53 (5), pp.509-513. ⟨10.1016/j.tetlet.2011.11.081⟩. ⟨hal-00868530⟩
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