State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, 210023, Nanjing, China.
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, 214122, Wuxi, Jiangsu, China.
Nat Commun. 2020 May 22;11(1):2572. doi: 10.1038/s41467-020-16477-1.
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-SOR. 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.
乙烯基硼酸酯和烷基硼酸酯是化学科学各个领域中多样化转化的关键组成部分。乙烯基硼酸酯和烷基硼酸酯的合成受到步骤繁琐和立体选择性差的限制。我们开发了一种受调控的自由基双官能化策略，用于构建含氟的乙烯基硼酸酯和烷基硼酸酯，使用集成的氧化还原活性试剂 IMDN-SOR。这种稳定的咪唑𬭩磺酸盐阳离子盐提供了一种可扩展且易于操作的方案，可高区域和立体选择性地对不饱和烃进行氟烷基化-硼化反应。产物可以进一步转化为有价值的氟化砌块。
