σ-Bond initiated generation of aryl radicals from aryl diazonium salts
Elene Tatunashvili, Bun Chan, Philippe E. Nashar, Christopher S. P. McErlean
Abstract
σ-Bond nucleophiles and molecular oxygen transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been illustrated in a variety of bond-forming reactions.
Topics & Concepts
ChemistryRadicalArylAryl radicalDiazonium CompoundsOxygenPhotochemistryOrganic chemistryPolymer chemistryAlkylRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods