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 34:55
Asymmetric Radical Multicomponent Couplings via Sensitization
DFT calculations elucidating stereoselectivity
CO2Me
MeO2C
CO2Me
CO2Me
suBe
N111.
N11..
AG ==2.5
Ni"-Ar
Ni".
reversible
stereodeterming
Ni-C bond
homolysis
planar, ground state
tetrahedral, excited-state
facile R.E.
Parallel cross-electrophile reaction at ground state
NCI analysis
NiCl2-DME (10 mol%)
(S,S)-sec-Bu-BiOx
Bu-Br
(13 mol%)
Mn, DMA, rt
CO2Me
dark
CO2Me
13% yield, 45% ee
Decreased yield and enantioselectivity with ground state Ni(II)
Noncovalent interactions are important to enantioselective control
J. Am. Chem. Soc. 2020, 142, 20390.
1
References
  • 1.
    L. Guo et al. (2020) General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis. Journal of the American Chemical Society
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