Umpolung Strategy for
Synthesis of β‑Ketonitriles
through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers
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Abstract
An
efficient method to synthesize β-ketonitriles from silyl
enol ethers by an umploung hypervalent iodine(III)–CN species
generated <i>in situ</i> from PhIO/BF<sub>3</sub>·Et<sub>2</sub>O/TMSCN has been developed for the first time. This method
can be applied to structurally diverse aromatic and aliphatic substrates
and further extended to preparation of bioactive compounds like 5-aminopyrazole
and 5-aminoisoxazole