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Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation

Weigang Zhang, Zhenlei Zou, Wenxuan Zhao, Shuo Lu, Zhengguang Wu, Mengjun Huang, Xiaochen Wang, Yi Wang (), Yong Liang (), Yi Zhu (), Youxuan Zheng and Yi Pan
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Weigang Zhang: Nanjing University
Zhenlei Zou: Nanjing University
Wenxuan Zhao: Nanjing University
Shuo Lu: Nanjing University
Zhengguang Wu: Nanjing University
Mengjun Huang: Nanjing University
Xiaochen Wang: Nanjing University
Yi Wang: Nanjing University
Yong Liang: Nanjing University
Yi Zhu: Jiangnan University
Youxuan Zheng: Nanjing University
Yi Pan: Nanjing University

Nature Communications, 2020, vol. 11, issue 1, 1-7

Abstract: Abstract Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. The synthesis of vinylboronates and alkylboronates suffers from step-tedious and poor stereoselective procedures. We have developed a regulated radical difunctionalization strategy for the construction of fluorine-containing vinylboronates and alkylboronates with an integrated redox-active reagent IMDN-SO2RF. This bench-stable imidazolium sulfonate cationic salt offers a scalable and operational protocol for the fluoroalkylation-borylation of unsaturated hydrocarbons in a high regio- and stereoselective manner. The products can be further transformed into valuable fluorinated building blocks.

Date: 2020
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DOI: 10.1038/s41467-020-16477-1

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