Login / Signup

Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization.

Da-Liang ZhuRuijie XuQi WuHai-Yan LiJian-Ping LangHong-Xi Li
Published in: The Journal of organic chemistry (2020)
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.
Keyphrases
  • energy transfer
  • visible light
  • room temperature
  • metal organic framework
  • quantum dots
  • reduced graphene oxide
  • oxide nanoparticles
  • heavy metals
  • gold nanoparticles
  • genetic diversity