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Transition-Metal-Free C -Diarylations to Reach All-Carbon Quaternary Centers.

Shobhan MondalBenjamin GunscheraBerit Olofsson
Published in: JACS Au (2024)
Herein, we disclose a convenient protocol for the α-diarylation of carbon nucleophiles to yield heavily functionalized quaternary products. Diaryliodonium salts are utilized to transfer both aryl groups under transition-metal-free conditions, which enables an atom-efficient and high-yielding method with broad functional group tolerance. The methodology is amenable to a wide variety of carbon nucleophiles and can be utilized in late-stage functionalization of complex arenes. Furthermore, it is compatible with a new class of zwitterionic iodonium reagents, which gives access to phenols with an ortho -quaternary center. The diarylated products bear an ortho -iodo substituent that can be utilized in further transformations, including the formation of novel, functionalized six-membered cyclic iodonium salts.
Keyphrases
  • transition metal
  • ionic liquid
  • randomized controlled trial
  • molecular dynamics
  • molecularly imprinted
  • simultaneous determination