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Synthesis of dibenzo[a,j]phenazine compounds using hemicucurbit[6]uril‐catalyzed oxidative dimerization of 2‐arylamines

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A supramolecular catalytic strategy for the synthesis of dibenzo[a,j]phenazine compounds from 2‐arylamines is demonstrated. The dimerization is achieved through the catalytic action of HemiQ[6] in an acidic environment. Kinetic constants… Click to show full abstract

A supramolecular catalytic strategy for the synthesis of dibenzo[a,j]phenazine compounds from 2‐arylamines is demonstrated. The dimerization is achieved through the catalytic action of HemiQ[6] in an acidic environment. Kinetic constants and activation energies have been calculated through UV/Vis spectrophotometric investigations using different amounts of HemiQ[6], whereby the reactivity was found to be related to the electron densities of the substrates. A possible mechanism involving host‐guest interaction between a 2‐arylaminium salt and HemiQ[6] through hydrogen‐bonding is proposed. The transformation of 2‐arylamines to dibenzo[a,j]phenazines in the presence of HemiQ[6] suggests that such supramolecular catalysis is effective for such constructions.

Keywords: synthesis dibenzo; dibenzo phenazine; dimerization; phenazine compounds

Journal Title: ChemCatChem
Year Published: 2020

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