Related Experiment Video
Updated: Apr 23, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Ag-catalysed double-benzylic isocyanation affording bisisonitriles and their utility as molecular linkers
Taiga Yurino1, Tomoko Ishikawa2, Takuya Nakamura2
1Division of Applied Chemistry and Frontier Chemistry Centre, Faculty of Engineering, Hokkaido University Sapporo 060-8628 Japan tyurino@eng.hokudai.ac.jp ohkuma@eng.hokudai.ac.jp.
Abstract:
We describe a Ag-catalysed nucleophilic double isocyanation at benzylic positions forming bisisonitriles. In the presence of a catalytic amount of Ag2O, bisdiphenylphosphinates or bisdiethylphosphates derived from the corresponding arenedimethanols successfully reacted with trimethylsilyl cyanide as a source of the isocyano group. A wide variety of bisisocyano-methyl arenes were obtained in moderate-to-high yields. The obtained bisisonitriles served as valuable molecular linkers using a Sc-catalysed multi-component reaction to afford light-emitting bis-3-amino-imidazo[1,2-a]pyridines.
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of Nitriles
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Cycloaddition Reactions: Overview
Electrophilic Aromatic Substitution: Nitration of Benzene

