Sulfoximine-Assisted Unsymmetrical Twofold C-H Functionalization of Arenes.

An unprecedented ruthenium (Ru)-catalyzed twofold unsymmetrical annulation of 3-O/N-allyl benzoic acid derivatives with isocyanates for the construction of dihydro-furan/indole-fused phthalimide scaffolds is discussed. This double-unsymmetrical functionalization of both o,o'-C-H bonds of arene moiety is explicitly viable under the influence of methylphenyl sulfoximine directing group constructing three different [C-C/C-C(O)/N-C(O)] bonds under a single catalytic system. A broad scope with all six-carbon-substituted arene motifs, control experiments, and gram-scale synthesis make the synthetic model viable and significant.