De-aromatization reactions of arenes have attracted considerable attention because they provide a simple way to synthesize functionalized alicyclic compounds, which can be used as intermediates for the preparation of natural products and bioactive compounds. [1] Over the past four decades, many methods, including oxidation, [2] reduction, [3] photocycloaddition, [4] [2,3] s-rearrangement, [5] electrophilic addition, [6] nucleophilic addition, [7] and other approaches [8] have been developed for breaking up the conjugated p system. The complexation of aromatic system to transition metals leads to the activation of arenes and thus facilitates the electrophilic addition of [M(h 2 -arene)] (M = Os, Re, Mo, and W) complexes and the nucleophilic addition of [M(h 6 -arene)] (M = Cr, Mn, and Ru) complexes.
We recently reported the facile palladium-catalyzed allylative de-aromatization reaction of benzylic chlorides 1 with allyltributytin. [9] This process appears to involve the formation and isomerization of the h 3 -allyl-h 3 -benzylpalladium intermediate 2 to give 2', which led to 3, where an allyl group is linked para to the exocyclic methylene group [Eq. ( 1)]. Our interest in extending the scope of this dearomatization reaction led us to examine the cinnamyl chloride 4. We assumed that, if the bis(h 3 -allyl)palladium