Triazolinediones as Highly Enabling Synthetic Tools
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- 作者：Kevin De Bruycker ; Stijn Billiet ; Hannes A. Houck ; Subrata Chattopadhyay ; Johan M. Winne ; Filip E. Du Prez
- 刊名：Chemical Reviews
- 出版年：2016
- 出版时间：March 23, 2016
- 年：2016
- 卷：116
- 期：6
- 页码：3919-3974
- 全文大小：2699K
- 年卷期：Kevin De Bruycker received his M.Sc. in chemistry from Ghent University, Ghent, Belgium, in 2013. His master thesis focused on reversible polymer systems based on the triazolinedione–indole ene reaction. Currently, he is pursuing his Ph.D. degree in the group of Prof. Filip Du Prez, conducting research on triazolinedione chemistry in interfacial systems.Stijn Billiet obtained a M.Sc. in chemistry at Ghent University, Ghent, Belgium in 2011, performing his master thesis in the Polymer Chemistry Research Group working on self-healing polymers. His Ph.D. research dealt with the development of a new click chemistry platform making use of triazolinediones. After a stay in the research group of Prof. Craig Hawker (University of California—Santa Barbara) in 2015, he obtained his Ph.D. degree in the beginning of 2016.Hannes A. Houck obtained both his B.Sc. (2012) and M.Sc. (2014) in chemistry from Ghent University, Ghent, Belgium. The subject of his master thesis revolved around the synthesis and modification of indole components and hence their tunable reversibility characteristics toward triazolinedione-based reactions. In 2015, he started postgraduate studies (Ph.D.) in a collaborative project under the supervision of Prof. Filip Du Prez at Ghent University and Prof. Christopher Barner-Kowollik at the Karlsruhe Institute of Technology, Karlsruhe, Germany.Subrata Chattopadhyay obtained his M.Sc. in chemistry in 2009 at the Indian Institute of Technology Madras, Chennai, India, and received his Ph.D. degree in 2014 at RWTH Aachen University, Aachen, Germany. During his Ph.D. research, he studied the synthesis and antimicrobial studies of azetidinium-functionalized polymers in the group of Prof. Möller. Afterwards, he joined the group of Prof. Du Prez as a postdoctoral researcher. His research interest focuses on sustainable design of functional polymers and nanomaterials, which includes the use of click-like reactions, renewable starting materials, reactions in water, and enzyme-catalyzed reactions.Johan M. Winne obtained a Ph.D. in chemistry from Ghent University in 2007, having studied cationic polyene cyclizations with Prof. Pierre De Clercq. He spent 2 years as a postdoctoral researcher with Prof. Gerald Pattenden at the University of Nottingham, Nottingham, UK, working on the total synthesis of terpenoid natural products. In 2009, he was appointed as doctor-assistant at Ghent University, and in 2015, he obtained a full-time independent faculty position. Besides maintaining active research interests in organic synthesis, aimed at biologically relevant applications, he has collaborated with the Polymer Chemistry Research Group to design and explore novel materials based on dynamic covalent chemistries.Filip E. Du Prez has headed since 1999 the Polymer Chemistry Research Group (www.PCR.UGent.be) at Ghent University, in which about 30 researchers are dealing with the development of new polymer structures, exploration of powerful functionalization methods (e.g., TAD chemistry), and the design of dynamic/renewable polymer materials for specific applications, such as vitrimers. In 2008, he had a visiting professor position at the CAMD Research Center (University of New South Wales, Sydney, Australia). He is author of about 200 peer-reviewed publications, 11 patents, and 10 book chapters and has been (co)chairman of 10 (inter)national conferences on polymer chemistry related topics. Since 2008, he is one of the editors of European Polymer Journal.
- ISSN：1520-6890
文摘
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.