Synthesis of aromatic molecules traditionally relies on the stepwise functionalization of a pre-existing arene. The dehydrogenation of (partially) saturated carbocycles represents a potentially attractive alternative method. A catalyst system consisting of a PdII salt in combination with a quinone co-catalyst has been developed for dehydrogenation of readily available cyclohexenes to afford arenes. This new catalyst system tolerates a wide range of functional groups and provides high yields and the broad substrate scope. The synthetic utility of the method is illustrated in the synthesis of a precursor to a TRPA1 (Transient Receptor Potential subfamily A1) activity modulator and dehydrogenation of an industrially relevant 1,3-cyclohexadiene.

Synthesis of substituted arenes via palladium-catalyzed aerobic dehydrogenation of cyclohexenes

246th National Meeting (2013)

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