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

Publication History

Received: 23 June 2020

Accepted after revision: 13 July 2020

Publication Date:
01 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

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苯并三唑的脱氮功能化研究进展

该手稿是为纪念已故的Rolf Huisgen教授在三唑化学上的杰出贡献而写的。

抽象

苯并三唑在有机合成中用作有用的合成子，由于它们独特的结构基序，它们能够在构建新键的过程中进行脱氮。近年来，已开发出各种方法将苯并三唑作为邻氨基苯二氮杂鎓的前体进行功能化，这些方法涉及过渡金属催化的偶联反应，主要是通过环化，硼化，烯基化，烷基化，羰基化和碳-杂原子键的形成。在这篇简短的综述中，我们主要关注苯并三唑在有机化学中通过脱氮过程进行的最新应用，并对其机理进行了讨论。

1引言

2种常见合成途径，可轻松获得苯并三唑衍生物

3 C–C键的形成

3.1环化反应

3.2丙烯酸化，链烯化，烷基化和羰基化反应

4碳-杂原子键的形成

5其他脱氮功能化

6结论和未来展望

出版历史

收到：2020年6月23日

修订后接受：2020年7月13日

发布日期：
2020年9月1日（在线）

©2020年。Thieme。版权所有

Georg Thieme Verlag
KGRüdigerstraße14，70469斯图加特，德国