A Simple One-Pot Synthesis of Silylated and Acylated Cyanohydrins

Cyanohydrins in Nature and the Laboratory: Biology, Preparations, and Synthetic Applications

“…Zinc iodide 11 or 18-crown-6 with potassium cyanide 12,13 are commonly used as catalysts for trialkylsilylcyanation: ytterbium tricyanide, 14 Lewis bases, 15 and other Lewis acids 16 have also been used. This method has been employed to prepare cyanohydrins of a wide variety of carbonyl compounds including sterically hindered ketones, 17,18 R,β-unsaturated compounds, 11,14,[19][20][21] easily enolizable ketones, and acid-sensitive ketones. 14 A fourth method of cyanohydrin preparation is transhydrocyanation from acetone cyanohydrin to the carbonyl compound.…”

Analogy of the Reactions of Aromatic and Aliphatic π-Electrophiles with Nucleophiles

“…We hypothesize that the electrophilic activity of aldehydes is higher, but we are not aware of any experimental evidence. The formation of benzoate of benzaldehyde cyanohydrine when KCN or LiCN is added to a mixture of benzaldehyde and benzoyl chloride is not sufficient [ 38 , 104 ].…”

“…This can be Further, adding nucleophiles to aliphatic π-electrophiles containing carbon-heteroatom double bonds that do not contain leaving groups is energetically favorable; hence, the usual protonation of the adducts provides stable products. This can be exemplified by the addition of cyanide anion to aldehydes and ketones that upon protonation form cyanohydrines or silylation O-silylated cyanohydrines (Scheme 15) [38,39]. Similarly, the addition of carbanions to aldehydes and ketones followed by protonation gives aldol-type products.…”

“…exemplified by the addition of cyanide anion to aldehydes and ketones that upon protonation form cyanohydrines or silylation O-silylated cyanohydrines (Scheme 15) [38,39]. Similarly, the addition of carbanions to aldehydes and ketones followed by protonation gives aldol-type products.…”

N,N-Dimethylpyridin-4-Amine Mediated Protocol for Cyanoethoxycarbonylation of Aldehydes Under Solvent-Free Conditions

“…Therefore, in recent days, acylcyanides and alkylcyanoformates are more preferred sources of cyanide as they are safer, effective and easily available [32][33][34][35][36][37]. These cyanide sources however, required the use of a base as catalyst to promote cyanation reaction [38][39][40][41][42][43][44][45][46][47][48][49][50]. In this direction, Poirier and co-workers [51,52] effectively utilized various tertiary amines as catalysts for the methoxycarbonylation of aldehydes whereas Deng and co-workers [53,54] have used a chiral base for the cyanocarbonylation of ketones.…”