Metal-free tandem carbene N-H insertions and C-C bond cleavages

A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/S E Ar/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage.