Qiuling Song, Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources, Fuzhou University, Fuzhou 350108, Fujian, China. E-mail: qsong@fzu.edu.cn
Abstract
Enantioselective assembly of chiral α-perfluoroalkylated organoboron compounds is a significant challenge in synthetic chemistry. Herein, a copper-catalyzed asymmetric B-H insertion reaction was employed to 2-arylpyridine-boranes with α-aryl-α-perfluoroalky diazomethanes, delivering over 40 novel chiral α-perfluoroalkylated organoboron compounds bearing boron/carbon vicinal stereogenic centers. This protocol accommodates a range of perfluoroalkyl substituents including CF₃, C₂F₅, C₃F₇ and C₄F₉. The reaction affords products in up to 85% yield, 99% ee, and dr >20:1 for longer-chain perfluoroalkyl substrates. Mechanistic insights are provided by deuterium-labeling and KIE experiments, together with reference to previous related precedents. The scalability and further transformations of the reaction products demonstrate their potential usefulness in synthetic community.
Keywords
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