ArticleChemistry (Weinheim an der Bergstrasse, Germany)2017
C-H Cyanation of 6-Ring N-Containing Heteroaromatics.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 41 citations in OpenAlex.
- Formal Synthesis ofMolecules (Basel, Switzerland) · 2026Article
- Unified ionic and radical C-4 alkylation and arylation of pyridines.Chemical science · 2024Article
- Late-Stage C-H Functionalization of Azines.Chemical reviews · 2023Review
- Direct Regioselective C-H Cyanation of Purines.Molecules (Basel, Switzerland) · 2023Article
- Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer.Journal of the American Chemical Society · 2021Article
- Pyridylphosphonium salts as alternatives to cyanopyridines in radical-radical coupling reactions.Chemical science · 2021Article
- Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A Strategy to Aminate Pyridines, Diazines, and Pharmaceuticals via Heterocyclic Phosphonium Salts.Organic letters · 2018Article
- C-H Cyanation of 6-Ring N-Containing Heteroaromatics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
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Authors and funding
15 authors at 4 institutions in 3 countries.
Funding
Abstract
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 trifluoromethanesulfinate 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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Registered trials
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