Carbodiimide-based synthesis of N-heterocycles: moving from two classical reactive sites to chemical bond breaking/forming reaction

Carbodiimides are a unique class of heterocumulene compounds that display distinctive chemical properties. The rich chemistry of carbodiimides has drawn increasing attention from chemists in recent years and has made them exceedingly useful compounds in modern organic chemistry, especially in the sy...

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Published inChemical Society reviews Vol. 49; no. 16; pp. 581 - 5849
Main Authors Wang, Yang, Zhang, Wen-Xiong, Xi, Zhenfeng
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 17.08.2020
Subjects
Carbodiimides
Chemical bonds
Chemical compounds
Chemical properties
Chemical synthesis
Chemists
heterocyclic nitrogen compounds
Organic chemistry
physicochemical properties
society
synthesis
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Summary:Carbodiimides are a unique class of heterocumulene compounds that display distinctive chemical properties. The rich chemistry of carbodiimides has drawn increasing attention from chemists in recent years and has made them exceedingly useful compounds in modern organic chemistry, especially in the synthesis of N-heterocycles. This review has outlined the extensive application of carbodiimides in the synthesis of N-heterocycles from the 1980s to today. A wide range of reactions for the synthesis of various types of N-heterocyclic systems (three-, four-, five-, six-, seven-, larger-membered and fused heterocycles) have been developed on the basis of carbodiimides and their derivatives. The extensive synthetic application of carbodiimides in various types of N-heterocyclic systems from the 1980s to today is outlined.
Bibliography:Zhenfeng Xi received his BSc from Xiamen University in 1983, MSc from Nanjing University, Zhengzhou University and the Henan Institute of Chemistry with Prof. Douman Jin in 1989, and PhD from the Institute for Molecular Sciences, Japan, with Professor Tamotsu Takahashi in 1996. He became an Assistant Professor at Hokkaido University in 1997. In 1998, he joined the College of Chemistry at Peking University, where he is now a Professor. His current research interest is focused on N
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Yang Wang received her BSc from China Agricultural University in 2008, and her PhD degree from Peking University with Professor Zhenfeng Xi and Professor Wen-Xiong Zhang in 2013. In 2013, she joined Professor Jieping Zhu's group as a Marie Curie postdoctoral fellow in EPFL, Switzerland. In 2017, she joined Professor Robert Britton's group as a postdoctoral fellow in SFU, Canada. In 2019, she joined the School of Medicine and Pharmacy at the Ocean University of China as an Associate Professor. Her research interests include development of novel synthetic methodologies towards bioactive N-heterocycles and natural products, and their medicinal chemistry.
activation and functionalization, for the synthesis of N-containing organic compounds directly from N
Wen-Xiong Zhang received his BSc from Hunan Normal University in 1996, his MSc from Guangxi Normal University in 1999, and his PhD from Nankai University with professor Li-Cheng Song in 2003. He carried out postdoctoral research at Peking University with Prof. Zhenfeng Xi and at Riken in Japan with Prof. Zhaomin Hou. In 2007, he joined the College of Chemistry at Peking University as an Associate Professor, where he is now a Professor. His research interests include design, synthesis and small molecule activation of rare-earth-metal heterocycles, metal-catalyzed C-N bond activation, and carbodiimide-based organic synthesis to construct N-containing heterocycles.
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ISSN:0306-0012
1460-4744
1460-4744
DOI:10.1039/c9cs00478e