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- Title
Gold(I)-Catalysed Direct Thioetherifications Using Allylic Alcohols: an Experimental and Computational Study.
- Authors
Herkert, Lorena; Green, Samantha L. J.; Barker, Graeme; Johnson, David G.; Young, Paul C.; Macgregor, Stuart A.; Lee, Ai‐Lan
- Abstract
A gold(I)-catalysed direct thioetherification reaction between allylic alcohols and thiols is presented. The reaction is generally highly regioselective (SN2′). 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.
- Subjects
GOLD catalysts; ALLYLIC alkylation; THIOLS; ALLYLATION; THERMODYNAMICS research
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 36, p11540
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201403293