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Insight into the second cyclopalladation of monopalladated azobenzenes by 1H NMR spectroscopy

Cyclopalladated complexes of azobenzenes have been widely studied primarily because of their application in organic synthesis, in the design of liquid crystalline materials as well as new catalysts, and bioactive compounds. Dicyclopalladated azobenzenes are one of the main focuses of our group since introducing the second palladium to investigated compounds broadens the scope of their applications and transformations. Although many azobenzene complexes with palladium have been prepared, information about the mechanism of those processes is still vague. Our previous study of cyclopalladation of azobenzenes by PdCl2(DMF)2 in DMF provided detailed insight into those reactions and proposed intramolecular C–H activation as the rate-determining step in both cyclopalladation reactions. As a continuation of this work, we decided to monitor the second cyclopalladation of monopalladated azobenzenes in DMF at 25 °C (Scheme 1) by 1H NMR spectroscopy that revealed monopalladated adduct as an intermediate in the investigated reactions.

Cyclopalladation ; Azobenzene ; 1H NMR ; Spectroscopy

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