Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 59, Pages 14733-14737Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703931
Keywords
cyanation; heterocycles; late-stage functionalization; nitriles
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Funding
- UCB Pharma
- Wellcome Trust ISSF [097813/Z/11/Z#]
- John Fell Fund of the University of Oxford
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Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C-H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoro-methanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
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