Direct Photoamination of Arenes with Ammonia and Primary Amines in the Presence of Electron Acceptors

Article abstract of DOI:10.1021/jo00381a009

Direct photoamination of phenanthrene, 9-methoxyphenanthrene, anthracene, naphthalene, and several substituted naphthalenes with ammonia or primary amines in the presence of m-dicyanobenzene occurs to give aminated dihydroarenes in fairly good yields. m-Dimethoxybenzene and biphenyl are photoaminated in lower yields.A suggested mechanism for the photoamination involves the nucleophilic attack of ammonia and amines on aromatic cation radicals generated by photochemical electron transfer to m-dicyanobenzene.The present photoamination is applied to direct introduction of various functionalized primary amines containing the vinyl, cyano, hydroxy, acetylamino, and ethoxycarbonyl groups.