Base-Metal Catalysis - presented by Prof. Lingling Chu and Assoc. Prof. Ming Joo Koh and Prof. Zhan Lu and Assoc. Prof. Tatsuhiko Yoshino and Prof. Naohiko Yoshikai

Base-Metal Catalysis

Lingling Chu, Ming Joo Koh, Zhan Lu and Tatsuhiko Yoshino

Prof. Lingling ChuAssoc. Prof. Ming Joo KohAssoc. Prof. Tatsuhiko YoshinoProf. Zhan Lu
Slide at 23:39
Asymmetric Radical Multicomponent Couplings via Chelation Chiral ligand design NiCl2 . DME (10 mol%) (S,S)-Biox (12 mol%) C4F9 I-C4F9 Mn, TMSCI, 1,4-dioxane, -10 °C 0%, NA 21%, 20:80 er 87%, 94:6 er Me Me 24%, 10:90 er 81%, 94:6 er 0%, NA 76%, 95:5 er (-10 °C) J. Am. Chem. Soc. 2020, 142, 9604.
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References
  • 1.
    H. Tu et al. (2020) Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling. Journal of the American Chemical Society
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Summary (AI generated)

After some initial exploration, we found that substituting oxalin with Linton, also known as au ligand, allowed for successful three-component coupling with 97 carbon or 99 carbon LT subsid. Additionally, using car ligand in August resulted in high yield and initial selectivity control for the three-component coupling.

We also investigated the use of commonly used steroid-demanding car ligands like pie box and box, which did not produce any product. This suggests that different reaction pathways may be involved in these reactions.

Optimizing the reaction conditions for three-component radical couplings showed a wide substrate scope, excellent functional groups, and a variety of areas for each of the three components. Under these optimal conditions, the NOFI cross cos delivered final products with high yield and ease.