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- W128776237 endingPage "1793" @default.
- W128776237 startingPage "1772" @default.
- W128776237 abstract "Hydrogen cyanide (HCN) is one of the most abundant feedstocks that undergoes catalyzed 1,2-additions to aldehydes, ketones, and imines. These reactions are catalyzed by Brønsted and Lewis acids, bases, and organocatalysts. Metal complexes of aluminum, yttrium, and lanthanides, and, even of late transition metals, are effective catalysts in these reactions. Preparatively useful procedures have been developed for the syntheses of enantiopure cyanohydrins and aminonitriles from the appropriate starting materials. Other useful reactions of HCN include conjugate addition to α,β-unsaturated carbonyl compounds and ring-opening reactions of epoxides and aziridines. Nickel-catalyzed hydrocyanation of 1,3-butadiene for the manufacture of adiponitrile is one of the largest homogeneously catalyzed reactions in the industry. Mechanistic studies related to this process helped to uncover many of the fundamental concepts in organometallic reaction mechanisms. These studies also led to an expansion of the scope of hydrocyanation to include alkenes and alkynes. This review will cover synthetic and mechanistic aspects of these reactions, including enantioselective versions, which have received surprisingly little attention. The scope and limitations of the current methodology for the hydrocyanation of different classes of alkenes, 1,3-dienes, and alkynes are discussed. Uses of trimethylsilyl cyanide and acetone cyanohydrin as safe surrogates for HCN are illustrated." @default.
- W128776237 created "2016-06-24" @default.
- W128776237 creator A5009350403 @default.
- W128776237 date "2014-01-01" @default.
- W128776237 modified "2023-09-27" @default.
- W128776237 title "5.36 Hydrocyanation in Organic Synthesis" @default.
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