Nickel-Catalyzed Cross-Electrophile Coupling Reactions for the Synthesis of <i>gem</i>-Difluorovinyl Arenes
Baojian Xiong, Ting Wang, Haotian Sun, Yue Li, Søren Kramer, Gui‐Juan Cheng, Zhong Lian
Abstract
A nickel-catalyzed cross-electrophile coupling reaction between (hetero)aryl bromides and 2,2-difluorovinyl tosylate is presented. This protocol provides facile incorporation of the gem-difluorovinyl moiety in organic molecules. The method features mild reaction conditions, good functional group tolerance, and excellent yields. Furthermore, mechanistic experiments and DFT studies indicate a Ni(0)/Ni(II) catalytic cycle, thus differing from the currently accepted catalytic cycle for nickel-catalyzed C(sp2)–C(sp2) cross-electrophile coupling reactions.
Topics & Concepts
CatalysisElectrophileNickelChemistryCoupling (piping)Coupling reactionCombinatorial chemistryPhotochemistryOrganic chemistryMaterials scienceMetallurgyFluorine in Organic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods