N-Heterocyclic Carbene-Nickel-Catalyzed Regioselective Diarylation of Aliphatic-1,3-Dienes

Aliphatic-1,3-dienes represent a problematic class of substrates for catalytic 1,2-dicarbofunctionalization due to inherent complications of undesired allylic rearrangement, consequently giving rise to inseparable isomeric product mixtures. Here, we show that aliphatic-1,3-dienes can participate in highly efficient and site-selective 1,2-diarylation, by merging with an aryl triflate and arylmetal reagent in the presence of a sizeable N-heterocyclic carbene (NHC)- Ni(0) catalyst. Adducts containing tertiary or quaternary centers and those derived from multifunctional bioactive molecules could be obtained.

Automated summary

The study demonstrates a new method for the highly efficient and site-selective 1,2-diarylation of aliphatic-1,3-dienes using N-heterocyclic carbene (NHC)-Ni(0) catalyst, allowing for the synthesis of products containing tertiary or quaternary centers.