Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

Article abstract of DOI:10.1016/j.tet.2014.02.083

A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF₃)₂ (PIFA), through a direct intramolecular oxidative C(sp²)-C(sp²) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.