HfCl4/NaBH4体系对亚砜的脱氧还原

Deoxygenation of Sulfoxides with HfCl4/NaBH4 System

摘要:

对HfCl4/NaBH4体系下亚砜的脱氧还原反应进行了研究。考察了溶剂、温度、摩尔比等因素对该反应的影响。实验结果表明，在HfCl4/NaBH4体系下，当溶剂为四氢呋喃（THF）、底物/HfCl4/NaBH4摩尔比=0.8/0.34/4.0时，亚砜回流反应0.6 h~1.5 h，脱氧还原得收率88%~99% 的硫醚产物。此外，在上述脱氧反应过程中，-NO2，-OMe，-F，-Cl，-Br等官能团具有兼容性。该方法对二苯基亚砜、二苄基亚砜尤为适合，收率高达98%~99%。

Abstract:

The deoxygenation of sulfoxides by HfCl4/NaBH4 system was investigated. The effect of reaction parameters, such as solvent, temperature, and molar ratio on the reduction was studied and discussed. According to the experimental result, when the solvent was tetrahydrofuran (THF) and the molar ratio of substrate/HfCl4/NaBH4 was 0.8/0.34/4.0, sulfoxides could be deoxygenated to sulfides in yields of 88%~99% by refluxing 0.6 h~1.5 h with HfCl4/NaBH4 system. Besides, in the oxygenation process，functional groups, such as -NO2, -OMe, -F, -Cl, and -Br groups were tolerated. This method was especially suitable for the deoxygenation of diphenyl sulfoxide and dibenzyl sulfoxide, and the yields were up to 98%~99%.