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...

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Bibliographic Details
Published in:ACS catalysis 2022-01, Vol.12 (1), p.724-732
Main Authors: Wang, Hongyu, Liu, Chen-Fei, Tan, Tong-De, Khoo, Kyna Ru Bin, Koh, Ming Joo
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c04766