Synthesis of phenanthridines by I2-mediated sp3 C-H amination.

An I2-mediated synthesis of phenanthridines via intramolecular sp3 C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected aniline substrates, and provides facile and efficient access to phenanthridine derivatives. This C-H amination protocol does not use transition metals, is operationally simple, and can be achieved on a gram scale.

Iodine-mediated oxidative N-N coupling of secondary amines to hydrazines.

An I2-mediated N-N coupling reaction has been established for oxidative dimerization of N-aryl aminopyridines to a variety of novel hydrazine derivatives under mild conditions. This synthetic method does not require use of transition metals and can be conveniently carried out on a gram scale. It is also applicable to diphenylamine and N-alkyl aniline substrates.