Exploiting 1,1-Dibromoalkenes as Direct Precursors to 5-Substituted 1,2,3-Triazoles

Abstract

Abstract1,1-Dibromoalkenes can be used as direct precursors to three classes of 5-substituted 1,2,3-triazoles. Three different approaches to 1,2,3-triazole products were developed, linked to the N1-substituent. Treatment of 1,1-dibromoalkenes with n-butyllithium and reaction with a sulfonyl azide gave 5-substituted 1-sulfonyl-1,2,3-triazoles. The use of lithium base followed by transmetalation to zinc and reaction with aryl azides allowed access to 1-aryl-1,2,3-triazoles. Finally, the use of EtMgBr as base and reaction with an alkyl azide formed 1-alkyl-1,2,3-triazoles.