Efficient approach to 1,1′-bisindoles via copper(i)-catalyzed double domino reaction

Abstract

A highly efficient copper(I)-catalyzed approach for the synthesis of 1,1′-bisindoles that is based on the formation of four bonds in one step has been developed. The unprecedented three component reaction between one molecule of a 1,2-bis(2-bromoaryl)hydrazine and two molecules of a 1,3-diketone employing 10 mol% CuI as a catalyst and Cs₂CO₃ as a base in DMSO at 100 °C for 24 h delivers substituted 1,1′-bisindoles with yields up to 92%. The new method proceeds as a double domino condensation/Ullmann type C–C coupling. It allows an efficient and practical access to substituted 1,1′-bisindoles in one step from easily available starting materials.