Highly selective sp C-N bond activation of tertiary anilines modulated by steric and thermodynamic factors

A highly selective sp 3 C-N cleavage of tertiary anilines was achieved using the TBN/TEMPO catalyst system. When N , N -diaklylanilines (alkyl, benzyl) were employed, the N-CH 3 bond was selectively cleaved via radical C-H activation. Moreover, when the allyl group was installed, totally reverse selectivity was observed. It is worth noting that the solvent effect is also crucial to obtain high reaction efficiency and selectivity. A highly selective sp 3 C-N cleavage of tertiary anilines was achieved using the TBN/TEMPO catalyst system.