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 18:11
Stereoselective Control of Radicals via Nickel Established mode for radical mediated Ni-catalyzed enantioselective couplings Challenge: reversible Ni-C bond homolysis renders facially selective addition impractical for asymmetric induction AG+ = 6.5 kcal/mol reversible Ni!! Ni-C bond homolysis favored radical homolysis preferential R.E. DKR via Curtin-Hammett principle Current approach: Reductive Elimination (R.E.) as the stereodetermining step Fu, G. C. * Science 2017, 356, eaaf7230; Jarvo, E. R.*. , Nat. Rev. Chem, 2017, 1. 65. 2014, 509, 299. Jamison, T. F. * Nature 2014, 509, 299.
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References
  • 1.
    J. Choi and G. C. Fu (2017) Transition metal–catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry. Science
  • 2.
    E. L. Lucas and E. R. Jarvo (2017) Stereospecific and stereoconvergent cross-couplings between alkyl electrophiles. Nature Reviews Chemistry
  • 3.
    S. Z. Tasker et al. (2014) Recent advances in homogeneous nickel catalysis. Nature
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Summary (AI generated)

The invention of reversible homely processes in products has inspired chemists like Greg Friman to develop elegant initial convergence across couplings. Electrophile couplings are impressive. However, the reversible feature also presents challenges in developing more efficient and asymmetric radical coupling modes. These modes aim to provide easier and higher precision control for efficient radical symmetrical couplings.