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Creators/Authors contains: "Uyeda, Christopher"

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  1. ; ; (, Chem)
    Azoalkanes can serve as radical precursors for various catalytic and stoichiometric C–C bond-forming reactions. However, their use in these processes is hampered by the complexity of their synthesis, which often requires multiple steps and strong oxidants. Here, we report a direct denitrogenative dimerization of tertiary alkyl azides to form azoalkanes. The reaction uses a dicobalt catalyst, which is uniquely effective in this transformation relative to analogous monocobalt catalysts and an isostructural dinickel catalyst. Critical to the N=N coupling reactivity is the formation of a dicobalt imido intermediate that is resistant to undergoing competing H-atom abstraction. The catalytic N=N coupling provides access to a broad scope of tertiary azoalkanes, and the resulting products can be used to form hindered C–C bonds between quaternary carbons. 
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    Free, publicly-accessible full text available February 1, 2026
  2. ; ; ; (, Journal of the American Chemical Society)
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  3. ; ; (, Journal of the American Chemical Society)
    Transition-metal-catalyzed reductive coupling reactions of alkynes and imines are attractive methods for the synthesis of chiral allylic amines. Mechanistically, these reactions involve an oxidative cyclization of the alkyne and the imine to generate a metallacyclic intermediate, which then reacts with H2 or an H2 surrogate to form the product. As an alternative to this hydrogenolysis pathway, here we show that transmetallation to zinc can occur, forming a zinc metallacycle product. This organozinc product serves as a versatile nucleophile for carbon–carbon and carbon–heteroatom coupling reactions. Mechanistic studies based on isotopic labelling experiments and DFT calculations suggest that the key transmetallation step occurs between a Co(II) species and ZnCl2. 
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  4. ; (, Chem Catalysis)
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  5. ; (, Accounts of Chemical Research)
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  6. ; ; (, Journal of the American Chemical Society)
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