Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?

The mechanism of the title reaction is found to consist of three steps by DFT calculations: (1) N(2) dissociation, (2) intramolecular Ag-carbene addition, and (3) proton transfer. The N(2) dissociation is turnover determining. The product 3-alkylideneoxindole is favored in tautomerization with 3-acetyl-2-hydroxyindole.

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