Silver(Ⅰ)-Catalyzed Of C4-H Amination Of 1-naphthylamine Derivatives

An efficient and simple protocol for the silver(I)-catalyzed C4-H amination of 1-naphthylamine derivatives with azodicarboxylates(DIAD)was explored at room temperature,affording the desire products in moderate to good yields(Scheme 1).The reaction could proceed under additive-and external-oxidant-free conditions.Generally,substituted 1-naphthyl amine derivatives,regardless of electron-withdrawing groups or electron-donating groups on the aryl ring,are well tolerated in the reaction.When the radical inhibitor such as 2,2,6,6-tetramethyl-1-piperindinyloxy(TEMPO)or 2,6-di-tert-butyl-4-methylphenol(BHT)was added into the amination reaction,the reaction inhibited successfully.And the adduct of BHT and azodicarboxylates(DIAD)as the product could be detected by HRMS.These results indicated that the reaction might proceed via a radical process.