Abstract
An effective and easy-to-handle process for the desulfitative Suzuki cross-couplings of arylsulfonyl chlorides and boronic acids in the presence of a recyclable polymer-supported NHC-Pd complex was developed. The supported catalyst could be reused several times with little loss of catalytic activity.
Key words
Suzuki reaction - N-heterocyclic carbene-palladium complex - polymer-supported catalysts - recyclable catalysts - arylsulfonyl chlorides
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General Procedure for the Suzuki Cross-Couplings of Arylsulfonyl Chlorides and Arylboronic Acids Catalyzed by the Polymer-Supported NHC-Pd Catalyst.
A 25 mL, round-bottom flask equipped with a magnetic stirring bar and a reflux condenser was charged with arylboronic acid (2 mmol), arylsulfonyl chloride (0.5 mmol), Na2 CO3 (1.5 mmol) and the polymer-supported NHC-Pd catalyst 1 (125 mg, 12.5 µmol Pd). The flask was connected to a vacuum line and then filled with argon (three times) before 5 mL THF was added. The resulting mixture was stirred and heated to reflux. After cooling to ambient temperature, the catalyst was filtered and washed with THF (3 × 4 mL), and then dried in vacuum for use in next run. The combined organic phase was dried over anhydrous MgSO4 , filtered and evaporated under reduced pressure. The product was purified by column chromatography.1 H NMR (400 MHz, CDCl3 ): δ = 7.23-7.28 (m, 1 H), 7.34 (d, J = 2.4 Hz, 1 H), 7.37-7.47 (m, 6 H). 13 C NMR (100 MHz, CDCl3 ): δ = 141.9, 138.1, 132.5, 131.1, 131.0, 130.8, 130.6, 129.6, 129.2, 126.4, 126.2, 126.1. MS (EI): m/z (%) = 222 (100) [M+ ], 186 (7), 152 (49).
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