6533b7d9fe1ef96bd126cd79
RESEARCH PRODUCT
Gold(I)-catalyzed intermolecular oxyarylation of alkynes: unexpected regiochemistry in the alkylation of arenes.
Ana B. CuencaGregori UjaqueKabir M. HossainSergi MontserratAgustí LledósGregorio AsensioMercedes Medio-simónGisela Manchasubject
inorganic chemicalsConcerted reactionOrganic ChemistryIntermolecular forceRegioselectivitychemistry.chemical_elementAlkylationPhotochemistryBiochemistrySulfurCatalysischemistryComputational chemistryElectrophileStructural isomerPhysical and Theoretical Chemistrydescription
The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel−Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-09-28 | Organic letters |