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Typical Experimental Procedure. To benzophenone oxime O-pentafluorobenzoate (0.1 mmol), E-β-styrylboronic acid (0.12 mmol), and CuTC (2 mg, 0.01 mmol) in a Schlenk tube flushed with argon was added dry DMF (2 mL). The reaction mixture was stirred at 50°C for 3 h and diluted with EtOAc (30 mL), The copper catalyst was removed by passing the reaction mixture through a short pad of silica gel that was buffered with triethylamine. After evaporation of the solvent, the residue was subjected to flash chromatography (silica gel, buffered by triethylamine, eluted with 40:1 hexanes/EtOAc) giving the desired product as a yellow oil in 90% yield.
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Typical Experimental Procedure. To benzophenone oxime O-pentafluorobenzoate (0.1 mmol), E-β-styrylboronic acid (0.12 mmol), and CuTC (2 mg, 0.01 mmol) in a Schlenk tube flushed with argon was added dry DMF (2 mL). The reaction mixture was stirred at 50°C for 3 h and diluted with EtOAc (30 mL), The copper catalyst was removed by passing the reaction mixture through a short pad of silica gel that was buffered with triethylamine. After evaporation of the solvent, the residue was subjected to flash chromatography (silica gel, buffered by triethylamine, eluted with 40:1 hexanes/EtOAc) giving the desired product as a yellow oil in 90% yield.
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The Beckmann rearrangement may be facilitated by the organostannane: reaction of the same substrate under the same reaction conditions with the analogous boronic acid does not cause formation of the Beckmann product
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The Beckmann rearrangement may be facilitated by the organostannane: reaction of the same substrate under the same reaction conditions with the analogous boronic acid does not cause formation of the Beckmann product.
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