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  • Title: Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization.
    Author: Zhu DL, Xu R, Wu Q, Li HY, Lang JP, Li HX.
    Journal: J Org Chem; 2020 Jul 17; 85(14):9201-9212. PubMed ID: 32527086.
    Abstract:
    An efficient method for visible-light-initiated, nickel-catalyzed Sonogashira C(sp)-C(sp2) 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.
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