Regiocontrolled halogen dance of 2,5-dibromopyrroles using equilibrium between dibromopyrrolyllithiums

Abstract

A regiocontrolled halogen dance reaction of 2,5-dibromopyrroles is described. An N,N-dimethylsulfamoyl group on the pyrrole nitrogen was especially effective for facilitating interconversion of the resulting 2,3- and 2,4-dibromopyrrolyllithiums, rendering the smooth halogen dance reaction. This method was applicable to the formal synthesis of atorvastatin.