Nickel-Catalyzed Sonogashira C(sp)–C(sp<sup>2</sup>) Coupling through Visible-Light Sensitization
Da‐Liang Zhu, Ruijie Xu, Qi Wu, Haiyan Li, Hai-Yan Li, Jian‐Ping Lang, Hong-Xi Li, Hong-Xi Li
Abstract
) coupling has been developed via an energy-transfer mode. Thioxanthen-9-one as a photosensitizer could significantly accelerate the arylation of alkynes with a wide range of (hetero)aryl halides in high yields. The cross-coupling reaction undergoes the stepwise oxidative addition of an arylhalide to nickel(0), transmetalation of the resulting aryl-Ni(II) halide species with Zn(II) acetylide into aryl-Ni(II) acetylide species, energy transfer from the excited state of thioxanthen-9-one to aryl-Ni(II) acetylide, and reductive elimination to the aryl alkyne.
Topics & Concepts
Sonogashira couplingAcetylideArylAlkynePhotochemistryChemistryAryl halideNickelReductive eliminationTransmetalationCatalysisHalideMedicinal chemistryPalladiumOrganic chemistryAlkylRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods