反应详情

温度

100 °C

An oven dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1.0 mol % Pd), 27 (7.4 mg, 0.015 mmol, 1.5 mol %), and NaOtBu (135 mg, 1.4 mmol). The tube was purged with argon and toluene (2 mL), 4-chlorotoluene (0.12 mL, 1.0 mmol), and benzylamine (0.165 mL, 1.5 mmol) were added through a rubber septum. The septum was replaced with a teflon screw cap, the tube was sealed, and the mixture was heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. A small amount of diarylated benzylamine was detected in the crude reaction mixture (GC ratio of product/diarylated benzylamine=16/1). The reaction mixture was cooled to room temperature, diluted with ether (20 mL), and extracted with 1 M HCl (5×40 mL). The organic phase was discarded and the combined aqueous extracts were basisified to pH 14 with 6M NaOH and extracted with ether (4×50 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give give 175 mg (89%) of a pale yellow oil.

1. customAn oven dried resealable Schlenk tube
2. customwas purged with argon
3. additionwere added through a rubber septum
4. customscrew cap
5. customthe tube was sealed
6. customhad been completely consumed
7. customreaction mixture (GC ratio of product/diarylated benzylamine=16/1)
8. temperatureThe reaction mixture was cooled to room temperature
9. extractionextracted with 1 M HCl (5×40 mL)
10. extractionextracted with ether (4×50 mL)
11. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customto give