Recent advances in radical-based C-N bond formation via photo-/electrochemistry

The employment of nitrogen sources with free N-H bonds for amination is considered to be most straightforward and desirable, especially when the C-N bonds are prepared from N-H bonds and non-functionalized carbon sources, such as C-H bonds and C-C double/triple bonds, since this obviates the needs f...

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Published inChemical Society reviews Vol. 47; no. 8; pp. 2591 - 268
Main Authors Zhao, Yating, Xia, Wujiong
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 23.04.2018
Subjects
Chemical bonds
Chemical synthesis
Cross coupling
Electrochemistry
Nitrogen
Reaction mechanisms
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Summary:The employment of nitrogen sources with free N-H bonds for amination is considered to be most straightforward and desirable, especially when the C-N bonds are prepared from N-H bonds and non-functionalized carbon sources, such as C-H bonds and C-C double/triple bonds, since this obviates the needs for the pre-installation of reactive groups in the starting materials and leads to a high atom and step economy. Recently, radical chemistry has been resuscitated owing to its great value in organic synthesis, and notable advances have been made in the direct use of N-H bonds for radical-based C-N bond formation with photo-/electrotechniques. Apart from the well-studied N-radical species addition pathway, radical-mediated aminations also proceed through N-atom nucleophilic addition, C-/N-radical cross-coupling, and a hydrogen-atom transfer (HAT) process. This review highlights the recent advances in this area with emphasis on the related reaction mechanisms. This review highlights the recent advances in cross-dehydrogenative amination for C-N bond construction from C-H/N-H cross-coupling partners through photocatalytic and/or electronic techniques.
Bibliography:Yating Zhao was born in Hunan Province, China, in 1989. She received her BS in Chemistry from Hunan Normal University in 2012. In the same year, she joined Prof. Xia's group at Harbin Institute of Technology, where she completed her PhD under the supervision of Professor Wujiong Xia in 2017. After that, she took a position at Quzhou University, China.
Wujiong Xia was born in 1975 in Zhejiang, China. He received his BS from the Chemistry Department of Lanzhou University in 1997, where he also received his PhD in 2002 under the supervision of Prof. Yongqiang Tu. Then, he joined the research group of John R. Scheffer at the University of British Columbia as a postdoctoral fellow. After his postdoctoral work, he returned to China in 2006 and worked at Harbin Institute of Technology as a full professor. In 2017, he moved to Harbin Institute of Technology at Shenzhen Campus. His research interests include UV/visible-light-promoted organic photochemical reactions, and the total synthesis of natural products.
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ISSN:0306-0012
1460-4744
DOI:10.1039/c7cs00572e