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Gold(I)‐Catalysed Direct Thioetherifications Using Allylic Alcohols: an Experimental and Computational Study
Author(s) -
Herkert Lorena,
Green Samantha L. J.,
Barker Graeme,
Johnson David G.,
Young Paul C.,
Macgregor Stuart A.,
Lee AiLan
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403293
Subject(s) - regioselectivity , allylic rearrangement , chemistry , substrate (aquarium) , catalysis , reaction conditions , reaction mechanism , combinatorial chemistry , computational chemistry , organic chemistry , oceanography , geology
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.