Nickel-Catalyzed C(Aryl)−O Bond Activation/Cross-Coupling Reaction of Carbazoles with Methyl Grignard: Synthesis of Ellipticine

A nickel‐catalyzed cross‐coupling reaction between methoxy‐substituted carbazoles and MeMgBr has been developed. This protocol for the cleavage of the C(aryl)−OMe was used to efficiently assemble various methyl‐substituted carbazoles and successfully applied to the total synthesis of the antitumor agent ellipticine. No wooden nickels here! An efficient method has been developed for a C(aryl)−O bond cleavage by employing a Ni‐catalyzed cross‐coupling reaction of methoxy‐substituted carbazoles with MeMgBr. This protocol was used to efficiently assemble various methyl‐substituted carbazoles and successfully applied towards the total synthesis of the antitumor natural product ellipticine, Cy=cyclohexyl.