简单亚胺的高效烯丙基化反应研究

Allylation Reaction of Simple Imines by Organotin Reagents

首次实现了In(OTf)3催化下二丁基二烯丙基锡对活性较低的简单亚胺的高效烯丙基化加成.烯丙基锡试剂和亚胺底物在10mol%的In(OTf)3催化下,无需添加其它辅助试剂,二氯甲烷中室温搅拌10h,就可以得到收率为80%～99%的高烯丙基胺产物.用四烯丙基锡替换该体系中的二丁基二烯丙基锡,50mol%用量即能得到很好的结果.同时还对反应的机理进行了探讨.

A new and effective allylation protocol was developed for less reactive simple imines using diallyldibutyltin in the presence of a catalytic amount of In（OTf）3. Allyltin reagents were reacted with imines in dichloromethane under 10 mol% In（OTf）3 without any other additives, to form homoallylic amines in moderate to good yields （80%-90%）. In addition, a series of aldimines could be reacted with tetraallyltin in a 2 ： 1 molar ratio catalyzed by In（OTf）3 （10 mol%） to afford the corresponding products in good yields. A probable mechanistic pathway to explain the allylation process was depicted.