Reactions involving first row divalent metal ions and O2 that result in oxidative aliphatic carbon-carbon (C-C) bond cleavage are of significant current interest in organic synthesis and in biology. Of relevance to synthesis, a brief summary of mechanistic studies of Cu(II)/O2-promoted aliphatic carbon-carbon bond cleavage reactivity within a coordinated diketonate ligand will be presented. The role of chloride anion in accelerating the oxygen activation step via the formation of a Cu–Cl species will be emphasized and compared with the chemistry found upon addition of carboxylate anion (e.g., benzoate). Model systems for acireductone dioxygenase enzymes will also be briefly discussed in the context of the observed metal ion-dependent regioselectivity in oxidative C-C bond cleavage reactivity.

M(II)/O2-dependent aliphatic carbon-carbon bond cleavage reactions

2019 Spring National Meeting

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