Advances in Skeletal Editing and Rearrangement Reactions - presented by Mamoru Tobisu and Assoc. Prof. Mark Levin and Prof. Corinna Schindler

Advances in Skeletal Editing and Rearrangement Reactions

Mamoru Tobisu and Mark Levin

MTAssoc. Prof. Mark Levin
Slide at 13:06
Catalytic Unimolecular Fragment Coupling (UFC) cat. Potential alternative to cross-coupling Late-stage bond formation through common functional groups X = CO X=CO2 X = SO2 X = NH (stoichiometric rxn) Wei et al. Tunge et al. Yorimitsu et al. Levin et al. Chem. Rev. 2021, 121, 365. Chem. Rev. 2011, 111, 1846. Org. Lett. 2018, 20, 6601. Nature 2021, 593, 223. cf. cross-coupling cat. -X + - MX
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References
  • 1.
    H. Lu et al. (2020) Selective Decarbonylation via Transition-Metal-Catalyzed Carbon–Carbon Bond Cleavage. Chemical Reviews
  • 2.
    J. D. Weaver et al. (2011) Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions. Chemical Reviews
  • 3.
    F. Takahashi et al. (2018) Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO2. Organic Letters
  • 4.
    S. H. Kennedy et al. (2021) Skeletal editing through direct nitrogen deletion of secondary amines. Nature
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Summary (AI generated)

CO and CO2 elimination can also be achieved through catalytic C and nitrogen deletion. One example of this is UFC, developed by Mark, which may serve as an alternative to cross coupling. UFC utilizes easily accessible starting materials and only requires catalysts, making it ideal for late-stage applications. However, the current scope of UFC is limited compared to cross coupling due to the necessity of breaking strong chemical bonds. To expand UFC's scope, a catalyst capable of activating strong chemical bonds like CO and CC bonds is required. Our research has focused on traditional metal-catalyzed reactions involving the activation of strong chemical bonds such as CEO bonds in AOLS and CC bonds of nitrous and many acids.