Ruthenium-Catalyzed ortho-C-H Mono- and Di-imidation of Arenes with N-Tosyloxyphthalimide

The Ru(II)-catalyzed imidation of the o-CH bond in arenes with N-tosyloxyphthalimide is realized with the assistance of a methyl phenylsulfoximine (MPS) directing group. This method is applicable to access the hitherto difficult o-CH di-imidation products. The sequential C-N and C-C bond formation of o-CH arenes creates peripherally decorated benzoic acid derivatives. The readily removable MPS-DG and easily modifiable phthaloyl moiety make this strategy synthetically viable for constructing highly functionalized C-N bearing arenes and heteroarenes.