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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-SO₂R_F. 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]

PMID: 32444596

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