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Rhodium(III)-Catalyzed Imidoyl C-H Activation for Annulations to Azolopyrimidines
Kim Søholm Halskov1, Michael R Witten1, Gia L Hoang1
1Department of Chemistry , Yale University , New Haven , Connecticut 06520 , United States.
Abstract:
Azolopyrimidines are efficiently prepared by direct imidoyl C-H bond activation. Annulations of N-azolo imines with sulfoxonium ylides and diazoketones under redox-neutral conditions and alkynes under oxidizing conditions provide products with various arrangements of nitrogen atoms and carbon substituents. We have also probed the mechanism of this first example of Rh(III)-catalyzed direct imidoyl C-H activation by structural characterization of a catalytically competent rhodacycle obtained after C-H activation and by kinetic isotope effects.
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