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Creators/Authors contains: "Bishop, Hayden D."

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  1. ; ; (, 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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