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?

Organic Chemistry Frontiers Pub Date: 2019-10-25 DOI: 10.1039/C9QO01049A

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.

Graphical abstract: 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
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