Efficient and mild swern oxidation using a new sulfoxide and bis(trichloromethyl)carbonate

Efficient and mild swern oxidation using a new sulfoxide and bis(trichloromethyl)carbonate
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使用新型亚砜和双(三氯甲基)碳酸酯进行高效、温和的斯沃恩氧化

DOI:
10.1080/00397911.2015.1137943
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发表时间:
2016-01
影响因子:
2.1
通讯作者:
Zhong, Weihui
Zhong, Weihui
中科院分区:
化学4区
文献类型:
--
作者:
Ye, Xiaojing;Fu, Hongliang;Ma, Jiahao;Zhong, Weihui

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摘要 设计并制备了一种新型亚砜,4-(2-(2-(甲基亚磺酰基)乙基)-4-硝基苯基)-吗啉(I),收率良好。当I与双(三氯甲基)碳酸酯结合时,伯醇和仲醇的Swern氧化在温和条件下得到显着促进,从而以良好的产率提供相应的醛或酮。值得注意的是,分离出的副产物硫化物V的再氧化可以在Swern氧化中进一步循环利用。图解摘要
ABSTRACT A new type of sulfoxide, 4-(2-(2-(methylsulfinyl) ethyl)-4-nitrophenyl)- morpholine (I), was designed and prepared in good yield. Upon the combination of I and bis(trichloromethyl)carbonate, the Swern oxidation of primary and secondary alcohols was significantly promoted under mild conditions, which afforded the corresponding aldehydes or ketones in good yields. It is noteworthy that the reoxidation of the isolated by-product sulfide V could be further recycled in Swern oxidation. GRAPHICAL ABSTRACT
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