Litcius/Paper detail

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

Weigang Zhang, Zhenlei Zou, Wenxuan Zhao, Shuo Lu, Zheng‐Guang Wu, Mengjun Huang, Xiaochen Wang, Yi Wang, Yong Liang, Yi Zhu, You‐Xuan Zheng, Yi Pan

2020Nature Communications56 citationsDOIOpen Access PDF

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-SO 2 R 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.

Topics & Concepts

StereoselectivityReagentRedoxCombinatorial chemistryChemistryOxidation reductionStereochemistryBiochemistryOrganic chemistryCatalysisFluorine in Organic ChemistryRadical Photochemical ReactionsWeb Data Mining and Analysis