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Triazolinediones as Highly Enabling Synthetic Tools

2016; American Chemical Society; Volume: 116; Issue: 6 Linguagem: Inglês

10.1021/acs.chemrev.5b00599

1520-6890

Kevin De Bruycker, Stijn Billiet, Hannes A. Houck, Subrata Chattopadhyay, Johan M. Winne, Filip Du Prez,

Chemical Synthesis and Analysis

Triazolinediones (TADs) are unique reagents in organic synthesis that have also found wide applications in different research disciplines, in spite of their somewhat "exotic" reputation. In this review, we offer two case studies that demonstrate the possibilities of these versatile and reliable synthetic tools, namely, in the field of polymer science as well as in more recently emerging applications in the field of click chemistry. As the general use of triazolinediones has always been hampered by the limited commercial and synthetic availability of such reagents, we also offer a review of the available TAD reagents, together with a detailed discussion of their synthesis and reactivity. This review thus aims to serve as a practical guide for researchers that are interested in exploiting and further developing the exceptional click-like reactivity of triazolinediones in various applications.