全氟丁基磺酸锡催化醛烯丙基化和Mukaiyama-aldol反应
收稿日期: 2012-09-22
修回日期: 2012-10-21
网络出版日期: 2012-11-02
基金资助
国家自然科学基金(Nos. 21172061, 21273068)资助项目.
Bisperfluorobutylsulfonate Bisbutyltin Catalyzed Allylation and Mukaiyama-aldol Reaction of Aldehyde
Received date: 2012-09-22
Revised date: 2012-10-21
Online published: 2012-11-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172061, 21273068).
二丁基二氯化锡与全氟丁基磺酸银在丙酮中室温反应, 得到二丁基二全氟丁基磺酸锡. 该配合物在空气中放置2 d, 1H NMR表明其结构未发生变化, TG-DSC表明在220 ℃是稳定的; 配合物C4F9SO3)2SnBu2能溶解在乙酸乙酯、丙酮、乙腈、四氢呋喃、乙醚等极性有机溶剂中, 但室温下, 在非极性溶剂己烷、二氯甲烷、甲苯中不溶. 以乙腈作溶剂, 室温下, (C4F9SO3)2SnBu2的用量分别为1.0和5.0 mol%, 醛的烯丙基化反应和Mukaiyama-aldol反应有效进行, 高产率得到对应产物.
关键词： 二丁基二全氟丁基磺酸锡; 醛的烯丙基化; Mukaiyama-aldol反应
刘毅 , 王勰 , 陈锦杨 , 李宁波 , 许新华 . 全氟丁基磺酸锡催化醛烯丙基化和Mukaiyama-aldol反应[J]. 有机化学, 2012 , 32(12) : 2328 -2333 . DOI: 10.6023/cjoc201209032
Bisperfluorobutylsulfonate bisbutyltin complex was successfully synthesized by treating C4F9SO3Ag with Bu2SnCl2 in acetone at room temperature. When the complex was exposed to air two days, 1H NMR spectra showed that its structure had no change. TG-DSC showed that the complex was stable below 220 ℃. The complex had a good solubility in polar solvents, such as ethyl acetate, acetone, acetonitrile, THF, ethyl ether. But it was poor soluble in hexane, CH2Cl2, toluene at room temperature. In the presence of 1.0 and 5.0 mol% of bisperfluorobutylsulfonate bisbutyltin respectively, allylation of aldehyde and Mukaiyama aldol reaction could efficiently occur in CH3CN at room temperature and give high yield of the corresponding products.
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