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Nickel Catalyzed Cross-Coupling of Aryl and Alkenyl Triflates with Alkyl Thiols

Regina M. Oechsner, Ivo H. Lindenmaier and Ivana Fleischer*

*Institute of Organic Chemistry, Faculty of Science, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany, Email: ivana.fleischeruni-tuebingen.de

R. M. Oechsner, I. H. Lindenmaier, I. Fleischer, Org. Lett., 2023, 25, 1655-1660.

DOI: 10.1021/acs.orglett.3c00218


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Abstract

A nickel catalyzed CS cross-coupling of aryl and alkenyl triflates with alkyl thiols provides a variety of thioethers under mild reaction conditions in short reaction time using an air-stable nickel precatalyst. The reaction offers a broad substrate scope, including pharmaceutically relevant compounds.

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proposed mechanism



General Procedure: Nickel-catalyzed C-S cross-coupling of aryl/alkenyl triflates and thiols for product isolation

A 25 mL inert, flame-dried and septum-caped Schlenk-tube equipped with a stirring bar was charged with KOAc (1.5 equiv.) and precatalyst XantphosNi(o-tolyl)Cl Ni (5 mol%). After addition of the respective thiol (1.1 equiv.) and the corresponding aryl/alkenyl triflate (1 mmol, 1.0 equiv.) the mixture was dissolved in dry THF (3 mL) under stirring. After 2 h at room temperature, the reaction mixture was quenched with brine (3 mL) and diluted with EtOAc (8 mL). The organic phase was washed with brine (5 mL) and the combined aqueous phases were re-extracted with EtOAc (3 × 10 mL). The combined organic phases were dried over MgSO4, concentrated in vacuo and purified by flash column chromatography (n-hexane/EtOAc).


Key Words

aryl sulfides, vinyl sulfides


ID: J54-Y2023