title: Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.
abstract: 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.
authors: Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS (UK).
authors: Lorena
authors: L
authors: Herkert
authors: Samantha L J
authors: SL
authors: Green
authors: Graeme
authors: G
authors: Barker
authors: David G
authors: DG
authors: Johnson
authors: Paul C
authors: PC
authors: Young
authors: Stuart A
authors: SA
authors: Macgregor
authors: Ai-Lan
authors: AL
authors: Lee
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D008958:Models, Molecular; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D020005:Propanols; D013440:Sulfides; C006463:allyl alcohol; D006046:Gold
keywords: allylation; allylic alcohols; gold; mechanism; thiols