醛的二氟亚甲基化

产物官能团类型


DAST

DAST试剂是一个亲核的氟化试剂,它于醛的反应相对温和。但是,该试剂在温度超过90 °C会发生分解。该反应的优选溶剂为二氯甲烷。

案例

To a suspension of the SM (150 mg, 0.302 mmol) in DCM (1.21 mL) was added DAST (0.100 mL, 0.754 mmol). The mixture was shaken at 50 °C for 30 min, after which time a yellowish solution resulted. To the mixture was added MeOH (~1 mL) and the solution was concentrated in vacuo. The resulting material was purified by column chromatography [25 g ultra snap column, 0-100% (76:24 EtOAc:EtOH)/(heptane)] to give 75 mg of 75% pure product. The material was repurified via RP-HPLC (5-95% ACN/H2O, 0.1% NH4OH throughout) to provide the product as a white solid. [34 mg, 22%]

Patent Reference: WO2015051043, page 91