Science of Synthesis

Ayaz, M.; De Moliner, F.; Morales, G. A.; Hulme, C., Science of Synthesis: Multicomponent Reactions, (2014) 1, 101.

Potassium and sodium cyanide are very common sources of cyanide ions. Although these compounds represent the most obvious substitutes for the hazardous and difficult-to-handle hydrogen cyanide, they still display high toxicity because of the generation of gaseous hydrogen cyanide that can occur if they are exposed to acidic solutions. Nevertheless, their use offers the simplest route to conduct a Strecker synthesis in an aqueous medium or in an ethanol/water mixture according to the original methodology that has been used for more than a century. The use of these salts in water in the presence of an acid (‌Scheme 4‌) effectively provides α-aminonitriles ‌1‌, typically in good to excellent yields with a broad substrate scope.[‌8‌] Conveniently enough, unreacted materials are efficiently removed by extractions and, since the byproducts are generally present in low amounts, the desired compounds can be subjected to subsequent synthetic steps without purification.

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References