Transition-Metal-Controlled Synthesis of 11<i>H</i>-Benzo[<i>a</i>]carbazoles and 6-Alkylidene-6<i>H</i>-isoindo[2,1-<i>a</i>]indoles via Sequential Intermolecular/Intramolecular Cross-Dehydrogenative Coupling from 2-Phenylindoles

Abstract

A catalyst-controlled synthesis of 11 H -benzo[ a ]carbazoles and 6-alkylidene-6 H -isoindo[2,1- a ]indoles is described. Pd(OAc) 2 favored 6-alkylidene-6 H -isoindo[2,1- a ]indoles via intramolecular C–H/N–H CDC reaction, while [Cp*RhCl 2 ] 2 led to 11 H -benzo[ a ]carbazoles through intramolecular C–H/C–H CDC reaction. Moreover, the synthesis of 11 H -benzo[ a ]carbazoles via sequential intermolecular ortho C–H/olefin coupling and intramolecular C3-H/olefin coupling from 2-phenylindoles and alkenes can be operated in one pot.