Palladium Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer (Pd _np -nSTDP) as Catalyst in the Synthesis of Mono-, Di-, and Trisulfides through C–S Cross-Coupling Reactions

Abstract

A wide variety of diaryl sulfides has been synthesized in excellent yields via C–S cross-couplings of aryl/heteroaryl halides with aromatic/heteroaromatic thiols in the presence of palladium nanoparticles immobilized on nanosilica triazine dendritic polymer (Pd _np -nSTDP) as a reusable catalyst under thermal conditions and microwave irradiation. Pd _np -nSTDP also showed excellent catalytic activity for the preparation of a series of di- and trisulfides with benzene, pyridine, pyrimidine, and/or 1,3,5-triazine as the central cores by one-pot multi C–S cross-coupling reactions.

Key words

supported catalysis - palladium - cross-coupling - dendrimers - thiols

• References and Notes

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• 22 The microwave system used in these experiments includes the following items: Micro-SYNTH Labstation, equipped with a glass door, a dual magnetron system with pyramid shaped diffuser, 1000 W delivered power, exhaust system, magnetic stirrer, ‘quality pressure’ sensor for flammable organic solvents, and a ATCFO fiber optic system for automatic temperature control.
• 23 General Procedure for the Synthesis of Diaryl Sulfides via C–S Cross-Coupling Catalyzed by Pd _np -nSTDP In a round-bottom flask equipped with a condenser and a magnetic stirrer, a mixture of aryl halide (1 mmol), aromatic/heteroaromatic thiol (1 mmol), K₂CO₃ (1.5 mmol), and Pd _np -nSTDP (0.05 mol% Pd) in DMF (2 mL) was stirred at 80 °C or irradiated with MW (230 W, 80 °C) for the desired time according to Table 2 and Scheme 2. The progress of the reaction was monitored by TLC (eluent: Et₂O–EtOAc, 5:1). After completion of the reaction, the mixture was cooled to r.t., Et₂O (15 mL) was added, and the catalyst was separated by centrifugation. The organic layer was washed with H₂O (2 × 10 mL) and dried over anhydrous MgSO₄. Filtration and evaporation of the solvent and purification of the crude product by recrystallization from Et₂O–EtOAc (5:1) afforded the pure product.
• 24 General Procedure for the Synthesis of Disulfides via Twofold C–S Cross-Coupling Catalyzed by Pd _np -nSTDP A mixture of 2,6-dibromopyridine (1 mmol), aromatic/heteroaromatic thiol (2 mmol), K₂CO₃ (2.5 mmol), and Pd _np -nSTDP (0.05 mol% Pd) in DMF (3 mL) was stirred at 80 °C or exposed to MW irradiation (230 W, 80 °C) for the appropriate time as mentioned in Table 3. The reaction progress was monitored by TLC (eluent: Et₂O–EtOAc, 3:1). After completion of the reaction, the mixture was cooled to r.t., EtOAc (10 mL) was added, and the catalyst was separated by centrifugation. The organic phase was washed with H₂O (2 × 10 mL), dried over anhydrous MgSO₄, filtered, and evaporated. The resulting crude product was purified by recrystallization from EtOAc to give the pure product.
• 25 General Procedure for the Synthesis of Trisulfides via Threefold C–S Cross-Coupling Catalyzed by Pd _np -nSTDP A mixture of aromatic trithiol (1 mmol), aryl bromide (3 mmol), K ₂ CO₃ (2.5 mmol), and Pd _np -nSTDP (0.05 mol% Pd) in DMF (3 mL) was stirred at 80 °C or subjected to MW irradiation (230 W, 80 °C) for the appropriate time according to Table 3. The workup was performed as mentioned for the synthesis of disulfides, and the pure trisulfide was obtained by recrystallization of the crude product from EtOAc.