Design of solid supported carbaborane catalyst with the aim of developing latent reactivity and reuse methods

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We developed a novel heterogeneous catalyst, solid supported carbaboranylmercuric triflate, with the aim of reutilizing it. This solid supported catalyst showed the remarkable reactivities for aryl allyl alcohol cyclization, cyclization of N-tosylanilinoallylic alcohols, regioselective cycloisomerization of aryl- and hetero-substituted 1,3-dienes, tandem carbocyclization, and etc. The workup of these reactions was very simple, as the catalyst was recovered by filtration of the reaction mixture through ordinary filter paper. Moreover, the recovered catalyst was reused without significant loss of activity at least 20 times. In the case of decreasing the activity of the recovered catalyst through the process of reuse, it could be reactivated via the reaction with 2N hydrochloric acid and then silver triflate.