Nickel-Catalyzed Intermolecular Carbobromination of Alkynes
Toshifumi Takahashi, Takuya Kurahashi, Seijiro Matsubara
Abstract
Organohalogen compounds such as alkenyl bromides are versatile and essential building blocks in organic synthesis. Herein, we describe the nickel-catalyzed intermolecular carbobrominations of alkynes with aryl bromides to form highly substituted and functionalized alkenyl bromides. The reductive elimination of the carbon–bromine bond from a Ni(II) species, which is usually a disfavored process, is achieved from a high-valent Ni(III) species in this reaction. This transformation not only expands the scope of transition-metal-complex-promoted bond-forming reactions but also, more particularly, accomplishes the formation of labile bonds, which is as challenging to achieve as the cleavage of inert bonds, such as C–O or C–H bonds.