Recent Developments on Denitrogenative Functionalization of Benzotriazoles

This manuscript is dedicated to the memory of the late Prof. Rolf Huisgen for his notable contributions on triazole chemistry.

Abstract

Benzotriazoles are employed as useful synthons in organic synthesis, and due to their unique structural motif, they are able to undergo denitrogenation during the construction of new bonds. Various methods for the functionalization of benzotriazoles as precursors of ­ortho-amino arenediazoniums have recently been developed that involve transition-metal-catalyzed coupling reactions, mainly via cyclization, borylation, alkenylation, alkylation, carbonylation and the formation of carbon–heteroatom bonds. In this short review, we primarily focus on the recent applications of benzotriazoles in organic chemistry that proceed via a denitrogenative process, and the mechanisms are also discussed.

1 Introduction

2 Common Synthetic Routes Allowing Easy Access to Benzotriazole Derivatives

3 Formation of C–C Bonds

3.1 Cyclization Reactions

3.2 Arylation, Alkenylation, Alkylation and Carbonylation Reactions

4 Carbon–Heteroatom Bond Formation

5 Miscellaneous Denitrogenative Functionalization

6 Conclusions and Future Perspectives

Key words

benzotriazoles - BtRC - ring cleavage - coupling reactions - denitrogenative functionalization

Publication History

Received: 23 June 2020

Accepted after revision: 13 July 2020

Article published online:
01 September 2020

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