Rh(III)-Catalyzed C–H Activation/Intramolecular Cyclization: Access to <i>N</i>-Acyl-2,3-dihydro-1<i>H</i>-carbazol-4(9<i>H</i>)-ones from Cyclic 2-Diazo-1,3-diketones and <i>N</i>-Arylamides

Abstract

High Resolution Image Download MS PowerPoint Slide A Rh(III)-catalyzed C–H activation/cyclization cascade reaction is described. The reaction involves cyclic 2-diazo-1,3-diketones and N -arylamides, and it proceeds via an intermolecular C–C bond formation and subsequent intramolecular C–N bond formation. A variety of N -acyl-2,3-dihydro-1 H -carbazol-4(9 H )-ones were obtained under mild conditions in good to excellent yields (65–90%). Key features of this strategy include high-efficiency, operational simplicity, scalability, and broad functional-group tolerance. In addition, H 2 O and N 2 are the only byproducts. Carbazole derivatives with free NH groups can be easily obtained through N -deprotection reactions.