Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 2, Pages 762-769Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302307y
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Nucleophilic aromatic substitution of 2- or 4-cyanoazines with the anions derived from aliphatic alpha,alpha-disubstituted esters and nitriles leads to displacement of the cyanide function. Enabling cyanides to be used as highly active leaving groups in SNAr reactions provides additional flexibility in starting materials for synthesis. We show that, in many cases, the cyanide leaving group is displaced preferentially in the presence of halogens. The resulting heteroaryl iodides, bromides, and chlorides subsequently can be used as handles for further chemical diversification.
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