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2.2.3.2.1 Use of Alkali Metal Cyanides as Cyanating Agents

DOI: 10.1055/sos-SD-213-00055

Ouali, A.; Taillefer, M.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014299.

Alkali metal cyanides, and particularly their potassium- and sodium-based representatives, have been widely used in the palladium-catalyzed cyanation of aryl iodides, bromides, and activated chlorides reported until the early 21st century.[‌10‌,‌11‌,‌19‌‌25‌] Due to their toxicity, handling of these cyanide sources requires specific safety precautions. The success of the cyanation is ensured by the choice of an appropriate concentration of cyanide ions and often the alkali metal cyanides have to be used together with greater than stoichiometric amounts of various additives such as potassium iodide,[‌11‌] alumina,[‌25‌] 18-crown-6,[‌21‌,‌22‌] or tedious-to-prepare phase-transfer-type phosphine ligands.[‌31‌]

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References


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