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Renaissance of Ring‐Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle
Author(s) -
Wang Yuanhao,
Wang Zhiguo,
Tang Yefeng
Publication year - 2020
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201900088
Subject(s) - chemistry , the renaissance , ring (chemistry) , diazo , reactivity (psychology) , imine , organic chemistry , combinatorial chemistry , catalysis , art history , medicine , art , alternative medicine , pathology
Abstract 1,2,3‐Benzotriazoles could undergo ring cleavage to form ortho ‐amino arenediazonium or α‐diazo‐imine species via a Dimroth‐type equilibrium. Historically, the synthetic potential of this unique reactivity had remained underdeveloped. Recently, some new strategies have been developed to effect the ring‐opening chemistry of benzotriazoles in more practical manners. A wide range of conceptually novel and synthetically useful reactions have been developed, which enable the access to diverse valuable heterocycles and ortho ‐amino arene derivatives. As one of the players in this field, our group has also contributed a series of intriguing transition‐metal‐catalyzed denitrogenative functionalizations of benzotriazoles. In this account, we aim to provide an overview of the ring‐opening chemistry of benzotriazoles, with a focus on relevant works published in the past decade. In order to show a whole picture of the research field, some pioneering works in its developing history will also be discussed briefly.