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Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 70℃; for 0.5 h; Schlenk technique Stage #2: With phenylsilane In 1-methyl-pyrrolidin-2-one at 70℃; for 30 h; Schlenk technique
General procedure: A tube-type Schlenk flask was charged with 0.045 mmol of catalyst D, 0.045 mmol of 1,8-diazabicyclo[5.4.0]undec-7-ene (7μL), and 1mL of N-methylpyrrolidone. The solution was stirred under nitrogen atmosphere at 60–70°C for 30 min. And, 2mL of N-methylpyrrolidone was added, followed by addition of a balloon charged with carbon dioxide gas. The solution was stirred at 60–70°C for 30 min. Then, 2-aminobenzenethiol derivatives (0.5 mmol), phenylsilane (1.5 mmol) dissolved in 0.5mL of N-methylpyrrolidone was added to the mixture. Reaction was carried out at 60–70°C for 18–30h. After the solution was cooled to room temperature, purification by flash chromatography on silica gel with n-hexane and ethyl acetate afforded benzothiazole derivatives.
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