Palladium-catalysed direct arylations of NH-free pyrrole and N-tosylpyrrole with aryl bromides

Bheeter, Charles Beromeo ; Bera, Jitendra K. ; Doucet, Henri (2012) Palladium-catalysed direct arylations of NH-free pyrrole and N-tosylpyrrole with aryl bromides Tetrahedron Letters, 53 (5). pp. 509-513. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2011.11.081

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Pyrroles; Aryl Bromides; C–H Activation; Catalysis; Palladium
ID Code:100029
Deposited On:27 Nov 2016 13:27
Last Modified:27 Nov 2016 13:27

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