Radical hydroboration for the synthesis of organoboron compounds
Organoboron compounds demonstrate diverse applications in the fields of organic synthesis, materials science, and medicinal chemistry. Compared to the conventional hydroboration reaction, radical hydroboration serves as an alternative approach for the synthesis of organoborons via different mechanis...
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| Published in | Chemical communications (Cambridge, England) Vol. 6; no. 32; pp. 4275 - 4289 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
16.04.2024
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Organoboron compounds demonstrate diverse applications in the fields of organic synthesis, materials science, and medicinal chemistry. Compared to the conventional hydroboration reaction, radical hydroboration serves as an alternative approach for the synthesis of organoborons
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different mechanisms. In radical hydroboration, a boryl radical is initially generated from homolytic cleavage of a B-H or a B-B bond, which is then added to an unsaturated double bond to deliver a carbon radical. Subsequent hydrogen atom transfer or reduction of the carbon radical to form a carbanion followed by protonation gave the final product. Over the past few years, numerous efforts have been made for efficient synthesis of boryl radicals and the expansion of substrate scope of the radical hydroboration reaction. Here, we discuss the recent advancement of radical hydroboration and its associated mechanisms. Numerous radical hydroboration strategies employing N-heterocyclic carbene borane, bis(pinacolato)diboron and pinacolborane as the boron source were illustrated. Thermochemical, photochemical and electrochemical strategies for the generation of boryl radicals were also discussed in detail.
This review describes the recent research on radical hydroboration, which covers different boron sources including N-heterocyclic carbene borane, bis(pinacolato)diboron and pinacolborane, as well as different strategies in boryl radical generation. |
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| Bibliography: | Yi-Feng Wang is a professor of Organic Chemistry at the Department of Chemistry, University of Science and Technology of China. He received his PhD in 2011 at the Nanyang Technological University, Singapore under the supervision of Profs. Koichi Narasaka and Shunsuke Chiba. He continued to work with Prof. Chiba as a research fellow (2011-2015) and was appointed as a Lee Kuan Yew Postdoctoral Fellow during 2012-2014. In 2015, he started his independent research work at USTC as a full professor. His research interests include radical chemistry, organoboron chemistry, and the synthesis of bioactive molecules. Yee Lin Phang received her Master of Science degree in Chinese Materia Medica at Shanghai University of Traditional Chinese Medicine, Shanghai, China, in 2022 under the supervision of Prof. Hongxi Xu and Prof. Changwu Zheng. Currently, she is a PhD candidate major in Organic Chemistry under the supervision of Prof. Yi-Feng Wang and Assoc. Prof. Feng-Lian Zhang at the University of Science and Technology of China, Hefei, China. Her research interest lies on the reactivity and application of Lewis-base boryl radicals. Feng-Lian Zhang is an associate professor of Organic Chemistry at the Department of Chemistry, University of Science and Technology of China. She received her BSc from Nankai University (P. R. of China) in 2011 and obtained her PhD from Nanyang Technological University, Singapore under the supervision of Prof. Shunsuke Chiba in 2016. After that she worked as a postdoctoral researcher at USTC (2016-2019), where she is now an associate professor. Her current focus is on organoboron chemistry, including methodology development and mechanistic investigation through computational studies. Ji-Kang Jin is a research associate of Organic Chemistry at Department of Chemistry, University of Science and Technology of China. He received his PhD in 2020 at University of Science and Technology of China, under the supervision of Prof. Yi-Feng Wang. After that he worked as a postdoctoral researcher at Jinan University (2020-2022). Currently, he worked as a research associate in Prof. Yi-Feng Wang's group at University of Science and Technology of China and his research interests include radical chemistry, organoboron chemistry, and medicinal chemistry. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-3 content type line 23 ObjectType-Review-1 |
| ISSN: | 1359-7345 1364-548X |
| DOI: | 10.1039/d4cc00398e |