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

2023/06/27 by Alistair Boyer, Matthew B. Williams, Matthew L. Martin +1
Chemistry · Biochemistry, Genetics and Molecular Biology · #Click Chemistry and Applications #Chemical Synthesis and Analysis #Cyclopropane Reaction Mechanisms

paper · doi:10.1055/s-0042-1751464

Abstract

Abstract 1,1-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.

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