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 14:28
Radicals in Chemical Synthesis Radical: versatile and empowering synthetic intermediate Reactivity orthogonal to cation or anion intermediates SOMO Nucleophilic radicals: carbon-centered radical HOMO Electrophilic radicals: heteroatom-centered radical Polarity matching effect; persistent radical effect unpaired electron open shell species Natural product synthesis Polymerization (ATRP) Photoredox catalysis Electrochemical synthesis [Ir(III)]* [Ir(II)] Procter, D. J.* et. al. Matyjaszewski, K.* et. al. MacMillan, D. W.C..* et. al. Little, R. D.* et. al. Nat. Rev. Chem. 2017, 1, 0077 Chem. Rev. 2001, 101, 2921 Chem. Rev. 2013, 113, 5312 Chem. Rev. 2022, 122, 3292
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References
  • 1.
    M. P. Plesniak et al. (2017) Radical cascade reactions triggered by single electron transfer. Nature Reviews Chemistry
  • 2.
    K. Matyjaszewski and J. Xia (2001) Atom Transfer Radical Polymerization. Chemical Reviews
  • 3.
    C. K. Prier et al. (2013) Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis. Chemical Reviews
  • 4.
    E. C. R. McKenzie et al. (2021) Versatile Tools for Understanding Electrosynthetic Mechanisms. Chemical Reviews
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Summary (AI generated)

The rapid development in the field of photos and electrochemical synthesis has led to advancements in radical chemistry. However, the high reactivity of radicals poses challenges to controlling their selectivity. Radicals have low barriers for reaction and can easily form undesired species through rapid diffusion. This makes controlling the selectivity of radicals difficult.

Chemists have made significant progress in understanding radical mechanisms and have developed catalytic methods using carboxylic acids or organic catalysts to control radical additions. This has led to efficient and powerful platforms for developing new and efficient radical couplings with high selectivity.

Despite these achievements, developing catalytic methods for asymmetrical radical couplings remains a challenge. N-catalysis is particularly interesting due to its low cost, abundance, versatility, and selectivity in radical couplings. This presents a promising avenue for eco-friendly catalysis.