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结构新颖的金属双核烯丙基试剂的合成及其芳香醛烯丙基化反应
引用本文:魏晓宁,柳凌艳,于磊,常卫星,李靖. 结构新颖的金属双核烯丙基试剂的合成及其芳香醛烯丙基化反应[J]. 高等学校化学学报, 2008, 29(4): 767-771
作者姓名:魏晓宁  柳凌艳  于磊  常卫星  李靖
作者单位:南开大学元素有机化学国家重点实验室,天津,300071;南开大学元素有机化学国家重点实验室,天津,300071;南开大学元素有机化学国家重点实验室,天津,300071;南开大学元素有机化学国家重点实验室,天津,300071;南开大学元素有机化学国家重点实验室,天津,300071
摘    要:报道了一个简捷的芳香醛的烯丙基化反应的新体系. 通过使用新型的金属双核烯丙基锡试剂(含有Sn—M键, M=Mn或Fe)与醛在二氯甲烷中反应, 无需使用任何辅助试剂, 直接得到较高产率(42%~98%)的高烯丙基醇. 实验结果证明过渡金属基团及M—Sn键具有相当高的活化锡原子上的烯丙基基团的作用.

关 键 词:金属双核烯丙基试剂  烯丙基化  
文章编号:0251-0790(2008)04-0767-05
收稿时间:2007-07-04
修稿时间:2007-07-04

New Binuclear Allylating Reagents for Allylation of Aromatic Aldehydes
WEI Xiao-Ning,LIU Ling-Yan,YU Lei,CHANG Wei-Xing,LI Jing. New Binuclear Allylating Reagents for Allylation of Aromatic Aldehydes[J]. Chemical Research In Chinese Universities, 2008, 29(4): 767-771
Authors:WEI Xiao-Ning  LIU Ling-Yan  YU Lei  CHANG Wei-Xing  LI Jing
Affiliation:State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China
Abstract:A new and simple methodology was reported for the allylation of aromatic aldehydes.In this protocol,new type of binuclear allylmetal reagents(with Sn-Mn,M=Mn or Fe)reacted with aldehydes in dichloromethane,without any other additives,to form homoallylic alcohols with yields from moderate to higher yields(42%-98%).Ample examples showed us that Tin-promoted carbonyl allylation is normally effected by either Sn(CH2CHCH2)4 or Bu3Sn(CH2CHCH2).In our work,we had synthesized three new binuclear compounds,a novel type of allylating reagent containing Sn-M bond(M=Mn or Fe).And it was found that they could also be applied in the allylation of aldehydes.This system owns the virtues of operational simplicity and more moderate condition.The allyl group in these binuclear compounds has been proved to be more reactive by the co-mediation of the transition metal groups and the bond formation of the M-Sn.
Keywords:Binuclear allylating reagent  Allylation  Aldehyde
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