Regioselective Knitting Of Aniline Via Ortho-c-n Bond Fusion Using Oso_4 As A Template

摘要

Synthesis of complicated molecules by using a simpler route is one of the important challenges to synthetic chemists. Transition metal mediated carbon-heteroatom bond formation reactions via C-H activation is a vital tool for achieving this goal. In this communication we disclose the first examples of OsO_4 mediated regioselective knitting of aniline moieties via ortho-C_(arom)-N fusion. Oxidation chemistry of anilines is varied, and its oxidative fusion reactions commonly give hydrazine, azo, or azoxy compounds. Because of its high electron-rich aromatic behavior, use of aniline as a coupling partner for C-N fusion reaction is rather unusual. However, metal mediated and/or electrochemical oxidative oligomerization of aniline to polya-nilines via para-C-N coupling has been long known. In comparison, similar multiple ortho-C-N fusion of aniline is not available in the literature.