The Combination of 1-Butyl-3-methylimidazolium Bromide and Trichloro(trifluoromethanesulfonato)titanium(IV) as a New Protocol for the Synthesis of Aryl Nitriles
Year: 2012
Type: article
Abstract: Nitriles are one of the most important precursors in organic synthesis. These compounds are used for the pre-paration of esters,1 amides,1,2 carboxylic acids,1,3 amines1,4 and thioamides.5 Nitriles have also found widespread ap-plication in preparation of heterocycles as tetrazoles.6 The classical method for the synthesis of alkyl nitriles is the reaction of alkyl halides with highly toxic metal cyanide via a nucleophilic pathway. However, this reaction induces one-carbon homologation. Recently, Togo and co-workers reported the conversion of alkyl halides into corresponding nitriles with retention of the number of carbon atoms by molecular iodine and DIH.7 Nitriles can also be obtained by the direct transformation of alcohols,8 aldehydes,9 carbox-ylic acids10 and aldoxime ethers,11 dehydration of amides,12 oxidation of primary amines13 and reduction of primary aliphatic nitro compounds.14 The dehydration of aldoximes is one of the most fundamental methods for the synthesis of nitriles. These reactions can be catalyzed by common reagents such as acid anhydrides,15 organic acids,16 strong mineral acids (H2SO4, ClSO3H), 17 NBS/pyridine,18 bromo-dimethylsulfonium bromide (BDMS),19 triflyl-imidazole20 and ion exchangers.21 Similarly, transition metal catalysts such as PtCl4(EtCN)2,
Language: English
Subfield: Catalysis
Field: Chemical Engineering
Domain: Physical Sciences
Open Access status: bronze
Funder: Islamic Azad University
OpenAlex ID: W2087859115