A highly efficient Hg(OTf)2-mediated Sakurai–Hosomi allylation of N-tert-butyloxycarbonylamino sulfones, aldehydes, fluoroalkyl ketones and α,β-unsaturated enones using allyltrimethylsilane

Abstract

It is reported that cheap and easily available Hg(OTf)₂ can efficiently mediate the Sakurai–Hosomi reaction of N-tert-butyloxycarbonyl (Boc) amino sulfones, aldehydes, and α-fluoroalkyl ketones using allyltrimethylsilane, with the catalyst loading down to 0.5–5.0 mol%, enabling the facile access to synthetically valuable homoallylic alcohols or amines, respectively. A chemoselective 1,4-allylation of α,β-unsaturated enones is also achieved under the catalysis of 5.0 mol% Hg(OTf)₂. In most cases, Hg(OTf)₂ exhibited intriguing properties superior to those of commonly used metal Lewis acids for such reactions, suggesting that mercury catalysis is worthwhile to explore.