A heterogeneous mercury salt catalyst stabilized by m-carbaborane

Abstract

Development of reusable heterogeneous catalysts has attracted a great deal of attention for both environmental and atom-economic reasons. In particular, a considerable amount of work has focused on reusable heavy- and rare-metal catalysts in order to limit the use and/or minimize the generation of problematic metal waste upon disposal. Herein is reported the development of a new polysiloxane-linked m-carbaboranylmercury (SiCB–Hg) catalyst, which can be used for various mercury salt-induced reactions such as the regioselective cyclization of 1,3-dienes and allyl alcohols, the intermolecular amination of allyl alcohols with sulfamates, and the cycloisomerization of alkynes. The catalyst can be completely recovered by simple filtration, with residual mercury in the filtrate <0.001% (nearly the quantitative limit). Furthermore, the catalyst can be reactivated by treatment with aqueous HCl and then AgOTf for reuse.