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Tandem Pd/Au-Catalyzed Route to alpha-Sulfenylated Carbonyl Compounds from Terminal Propargylic Alcohols and Thiols
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 8, 2159-2163 p.Article in journal (Refereed) Published
Abstract [en]

An efficient and highly atom-economical tandem Pd/Au-catalyzed route to -sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at the -position of the alcohol. Both aromatic and aliphatic thiols generated the -sulfenylated carbonyl products in good to excellent yields. A mechanism is proposed in which the reaction proceeds through a Pd-catalyzed regioselective hydrothiolation at the terminal triple bond of the propargyl alcohol followed by an Au-catalyzed 1,2-hydride migration.

Place, publisher, year, edition, pages
2014. Vol. 20, no 8, 2159-2163 p.
Keyword [en]
atom efficiency, gold, palladium, sulfenylated carbonyl, tandem catalysis
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:uu:diva-222173DOI: 10.1002/chem.201304111ISI: 000330903700007OAI: oai:DiVA.org:uu-222173DiVA: diva2:711505
Available from: 2014-04-10 Created: 2014-04-08 Last updated: 2017-12-05Bibliographically approved

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Biswas, SrijitSamec, Joseph S. M.

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