2019 Volume 77 Issue 10 Pages 982-993
Mercuric trifluoromethanesulfonate [Hg(OTf)2] with high reactivity toward carbon-carbon multiple bonds has been widely used as a well-known mercury reagent for organic synthesis. On the basis of the catalytic mechanism of Hg(OTf)2 in the hydration of alkynes, we have developed new catalytic systems using the salt-metathesis reaction of Hg(OAc)2/Sc(OTf)3, PhHgOAc/HOTf, m-carbaboranylmercury chloride (m-CBHgCl)/AgOTf, which can achieve C-C bond-forming cyclizations, heterocycle synthesis and cyclization initiated by 1,3-dienes at high catalytic turnovers under mild conditions. To further enhance the usability as well as synthetic utility of the catalytic systems, the solid-supported mercuric salts (Si-PhHgOTf and Si-CBHgOTf) were developed and found to act as powerful catalyst for most mercury salt-catalyzed reactions. These heterogeneous catalysts were recovered without serious mercury leakage by simple filtration.
