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. 2017 Aug 18;22(8):1367.
doi: 10.3390/molecules22081367.

Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions

Sumbal Saba  1   2 , Giancarlo Vaccari Botteselle  3 , Marcelo Godoi  4 , Tiago Elias Allievi Frizon  5 , Fábio Zazyki Galetto  6 , Jamal Rafique  7 , Antonio L Braga  8
Affiliations

Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions

Sumbal Saba et al. Molecules. .

Abstract

The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and 3 equiv. of DMSO, under microwave irradiation. This new protocol allowed the preparation of several unsymmetrical diorganyl chalcogenides in good to excellent yields.

Keywords: CuI; boronic acid; cross-coupling; selenide; selenium; solvent-free; telluride; tellurium.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Solvent- and ligand-free synthesis of unsymmetrical diorganyl chalcogenides catalyzed by CuI.
Scheme 2
Scheme 2
Synthesis of unsymmetrical organotellurides a,b. a Reaction conditions: 1 (0.25 mmol), 2 (0.5 mmol) in the presence of CuI (3.0 mol %) and DMSO (3.0 equiv.) applied for 15 min at 100 °C with 100 W of MW-irradiation; b Isolated yields.
Scheme 3
Scheme 3
Synthesis of unsymetrical organoselenides and sulfides a,b. a Reaction conditions: 4 or 5 (0.25 mmol), 2 (0.5 mmol) in the presence of CuI (3.0 mol %) and DMSO (3.0 equiv.) for 15 min at 100 °C and 100 W of MW-irradiations; b Isolated yields.
Scheme 4
Scheme 4
Scale-Up of the reaction.
Scheme 5
Scheme 5
Control experiments for reaction mechanism. (a) Reaction in the presence of radical inhibitor; (b) Reaction under inert atmosphere; (c) Reaction under oxygen atmosphere.
Scheme 6
Scheme 6
A plausible reaction pathway.
See this image and copyright information in PMC

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