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Issue 8, 2011
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An improved catalyst architecture for rhodium(III) catalyzed C–H activation and its application to pyridone synthesis

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Abstract

We have developed a method for preparing pyridones from the coupling reaction of acrylamides and alkynes with either stoichometric Cu(OAc)2 or catalyticCu(OAc)2 and air as oxidants. In the course of these studies, it was found that a larger ligand, 1,3-di-tert-butylcyclopentadienyl (termed Cpt) results in higher degrees of regioselectivity in the alkyneinsertion event. The transformation tolerates a broad variety of alkynes and acrylamides. Furthermore, Cpt and Cp* demonstrate similar catalytic activity. This similarity allows for mechanistic studies to be undertaken which suggest a difference in mechanism between this reaction and the previously studied benzamide system.

Graphical abstract: An improved catalyst architecture for rhodium(iii) catalyzed C–H activation and its application to pyridone synthesis

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Publication details

The article was received on 12 Apr 2011, accepted on 28 Apr 2011 and first published on 16 May 2011


Article type: Edge Article
DOI: 10.1039/C1SC00235J
Citation: Chem. Sci., 2011,2, 1606-1610
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    An improved catalyst architecture for rhodium(III) catalyzed C–H activation and its application to pyridone synthesis

    T. K. Hyster and T. Rovis, Chem. Sci., 2011, 2, 1606
    DOI: 10.1039/C1SC00235J

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