Rhodium(III)-Catalyzed Imidoyl C–H Activation for Annulations to Azolopyrimidines

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 substi...

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Bibliographic Details
Published in:Organic letters 2018-04, Vol.20 (8), p.2464-2467
Main Authors: Halskov, Kim Søholm, Witten, Michael R, Hoang, Gia L, Mercado, Brandon Q, Ellman, Jonathan A
Format: Article
Language:English
Subjects:
Alkynes
Azo Compounds
carbon
carbon-hydrogen bond activation
Catalysis
chemical bonding
chemical reactions
chemical structure
imines
isotopes
Molecular Structure
nitrogen
Oxidation-Reduction
Pyrimidines - chemical synthesis
Rhodium
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.8b00816