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Synthesis 2020; 52(24): 3781-3800
DOI: 10.1055/s-0040-1707253
DOI: 10.1055/s-0040-1707253
short review
Recent Developments on Denitrogenative Functionalization of Benzotriazoles
G.Y. sincerely thanks the National Natural Science Foundation of China (Grant No. 21572094) and the Natural Science Foundation of Zhejiang Province (Grant No. LY18B020005) for financial support. V.K.T. gratefully acknowledges the Science Engineering and Research Board (SERB), New Delhi (Grant No. EMR/2016/001123) for the funding.
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 functionalizationPublication History
Received: 23 June 2020
Accepted after revision: 13 July 2020
Article published online:
01 September 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
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