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An Improved Catalyst Architecture for Rhodium (III) Catalyzed C-H Activation and its Application to Pyridone Synthesis.

ABSTRACT: We have developed a method for preparing pyridones from the coupling reaction of acrylamides and alkynes with either stoichometric Cu(OAc)2 or catalytic Cu(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 alkyne insertion 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.

SUBMITTER: Hyster TK

PROVIDER: S-EPMC4286810 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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An Improved Catalyst Architecture for Rhodium (III) Catalyzed C-H Activation and its Application to Pyridone Synthesis.

Hyster Todd K TK Rovis Tomislav T

Chemical science 20110801 8

We have developed a method for preparing pyridones from the coupling reaction of acrylamides and alkynes with either stoichometric Cu(OAc)2 or catalytic Cu(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 alkyne insertion event. The transformation tolerates a broad variety of alkynes and acrylamides. Furthermore, Cp ...[more]

PMID: 25580208

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