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


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.

SUBMITTER: Zhang W 

PROVIDER: S-EPMC7244735 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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

Zhang Weigang W   Zou Zhenlei Z   Zhao Wenxuan W   Lu Shuo S   Wu Zhengguang Z   Huang Mengjun M   Wang Xiaochen X   Wang Yi Y   Liang Yong Y   Zhu Yi Y   Zheng Youxuan Y   Pan Yi Y  

Nature communications 20200522 1


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-SO<sub>2</sub>R<sub>F</sub>. This bench-stable imidazolium sulfonate cationic  ...[more]

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