Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Aug 2019, accepted on 25 Oct 2019 and first published on 25 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01049A
Org. Chem. Front., 2019, Advance Article

  •   Request permissions

    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

    Y. Gong, Z. Cao, Y. Shi, F. Zhou, Y. Zhou and J. Zhou, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01049A

Search articles by author

Spotlight

Advertisements