Ag-catalysed double-benzylic isocyanation affording bisisonitriles and their utility as molecular linkers

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.