A new and convenient protocol for the catalytic dehydration of aromatic and aliphatic amides using silanes in the presence of catalytic amounts of fluoride is presented. The synthesis of aliphatic and aromatic nitriles proceeds with high selectivity under mild conditions. Notably, a wide substrate range is converted in good to excellent yields.

The synthesis of benzimidazoles by intermolecular cyclization reaction of 2-iodoanilines with nitriles has been developed. These reactions proceeded without the aid of any transition metals or ligands and just using KOBu(t) as the base. A variety of substituted benzimidazole derivatives can be synthesized by the approach.

A new strategy has been developed for the benzylation of nitriles directly from benzyl alcohols. In this process benzyl alcohols undergo retro-Claisen activation with cyanoacetic esters to generate an active electrophile and a carbanionic nucleophile. In the presence of Pd(0) these intermediates undergo catalytic coupling to generate a new C-C bond, resulting in the formation of phenyl propioni...

Allyl amides were synthesised from the reaction of allyl alcohols and halogenated nitriles using a platinum multifaceted catalysis approach in which both the nucleophilic addition and subsequent [3,3]-sigmatropic rearrangement steps of the process were catalysed by the same complex. Additionally, (1)H/(13)C{(1)H} NMR and GC studies provided the first insights into the mechanism of this transfor...

We report the simultaneous imaging of protonated and deprotonated forms of carbonylcyanide p-trifluoromethoxy-phenylhydrazone (FCCP) molecules in live cells by Raman microscopy. Nitriles, structure-sensitive Raman tags, are used to detect the two distinct molecular structures, demonstrating the potential of Raman microscopy for structure-based imaging of bioactive small molecules.

The copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate furnishes aromatic nitriles in moderate to good yields. The cascade process involves a copper-catalyzed aerobic C-H oxidation, a retro-cyanohydrination, and a copper-catalyzed aerobic oxidative C-H functionalization.

A novel, three-component C-C, C-N and C-O bond forming reaction is described. In the presence of 20 mol% CuO, this condensation reaction of CF3CHN2, nitriles, and aldehydes proceeds to afford CF3-substituted oxazolines in moderate to high yields with excellent diastereoselectivities. Subsequent ring-opening of oxazolines gives rise to the corresponding vicinal amino alcohols.

Trifluoromethanesulfonic acid and other electrophiles promote formation of the adamantanone core from the readily accessible 1,5-dimethyl-3,7-dimethylenebicyclo[3.3.1]nonan-9-one 2. Because adamantyl cation 3 can be trapped by a range of nucleophiles, including aromatic and heteroaromatic rings, alcohol, nitriles, and halides, access to a wide variety of functionality at the newly formed tertia...

An efficient and environmentally friendly methodology for the solvent-free synthesis of α-amino nitrile derived ureas from α-amino acid based amino nitriles has been developed. At room temperature no epimerization was observed in the resulting ureas, but under microwave heating, epimerization occurred at the chiral center bearing the cyano group.