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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