Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.


Journal Article

A gold(I)-catalysed direct thioetherification reaction between allylic alcohols and thiols is presented. The reaction is generally highly regioselective (S(N)2'). This dehydrative allylation procedure is very mild and atom economical, producing only water as the by-product and avoiding any unnecessary waste/steps associated with installing a leaving or activating group on the substrate. Computational studies are presented to gain insight into the mechanism of the reaction. Calculations indicate that the regioselectivity is under equilibrium control and is ultimately dictated by the thermodynamic stability of the products.

Full Text

Cited Authors

  • Herkert, L; Green, SLJ; Barker, G; Johnson, DG; Young, PC; Macgregor, SA; Lee, A-L

Published Date

  • September 2014

Published In

Volume / Issue

  • 20 / 36

Start / End Page

  • 11540 - 11548

PubMed ID

  • 25080400

Pubmed Central ID

  • 25080400

Electronic International Standard Serial Number (EISSN)

  • 1521-3765

International Standard Serial Number (ISSN)

  • 0947-6539

Digital Object Identifier (DOI)

  • 10.1002/chem.201403293


  • eng