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.
Highlights
Transition metal-catalyzed coupling reactions are among the most commonly applied protocols for the preparation of various target molecules under mild conditions [1,2]
In connection with our continuing interest in designing and developing eco-friendly processes and cross-coupling reactions, [59,60,61,62,63,64], we describe a straightforward method for the processes and cross-coupling reactions, [59,60,61,62,63,64], we describe a straightforward method for synthesis of unsymmetrical diorganyl-chalcogenides (S, Se and Te) through the reaction of boronic the synthesis of unsymmetrical diorganyl-chalcogenides (S, Se and Te) through the reaction of boronic acids and half equiv. of diorganyl dichalcogenides, employing CuI as a catalyst, under solvent- and acids and half equiv. of diorganyl dichalcogenides, employing CuI as a catalyst, under solvent- and ligand-free conditions (Scheme 1)
We evaluated catalyst loading boronic acid (2a) were (entries used as model substrates (Table 1)
Summary
Transition metal-catalyzed coupling reactions are among the most commonly applied protocols for the preparation of various target molecules under mild conditions [1,2]. Organoboronic acids have become interesting and appropriate alternative compounds for the preparation of symmetrical and unsymmetrical diaryl organochalcogenides via compounds for the preparation of symmetrical and unsymmetrical diaryl organochalcogenides via cross-coupling transformations In this regard, Wang and Tanigushi, independently reported the preparation of diorganyl. Indium [47], iron [48], copper [49,50,51,52,53,54,55] and silver [56] Most of these procedures have their particular drawbacks, such as the use of ligands, reducing agents, air sensitivity, long reaction time, and/or the use of toxic solvents.
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