jo0c01010_si_003.cif (654.24 kB)
Sulfoximine-Assisted Unsymmetrical Twofold C–H Functionalization of Arenes
datasetposted on 2020-06-22, 09:30 authored by Koushik Ghosh, Arghadip Ghosh, Kallol Mukherjee, Raja K. Rit, Akhila K. Sahoo
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.
Ruinfluencedihydro-furanFunctionalizationTwofoldacidcontrol experimentsderivativemethylphenyl sulfoximinearene moietyArenerutheniumSulfoximine-Assistedsix-carbon-substituted arene motifsisocyanateunsymmetrical annulationconstructionscopegram-scale synthesisUnsymmetricalbenzoicphthalimide3-modelscaffolddouble-unsymmetrical functionalizationbond