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

Zhang, Weigang; Zou, Zhenlei; Zhao, Wenxuan; Lu, Shuo; Wu, Zhengguang; Huang, Mengjun; Wang, Xiaochen; Wang, Yi et al. · Nat Commun · 2020

basic_science · Level V

Where this comes from

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<sub>2</sub>R<sub>F</sub>. 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.