Metzger Albrecht, Schade Matthias A, Manolikakes Georg, Knochel Paul
Department Chemie, Ludwig-Maximilians-Universität München, Germany.
Chem Asian J. 2008 Sep 1;3(8-9):1678-91. doi: 10.1002/asia.200800161.
A new method for the preparation of highly functionalized benzylic zinc chlorides by the direct insertion of zinc dust into the corresponding benzylic chlorides in the presence of LiCl is described without the formation of homocoupling products (<5 %). Various reactions of these benzylic zinc reagents with a broad range of electrophiles, which lead to polyfunctionalized products, are reported. In particular, the cross-coupling reactions of the benzylic zinc chlorides with aromatic chlorides, bromides, and tosylates in the presence of [Ni(acac)(2)] (acac=acetylacetonate) and PPh(3) proceeded in good to excellent yields to give the corresponding diaryl and heterodiaryl methanes.
描述了一种在LiCl存在下通过将锌粉直接插入相应的苄基氯化物中来制备高官能化苄基氯化锌的新方法,该方法不会形成均偶联产物(<5%)。报道了这些苄基锌试剂与多种亲电试剂的各种反应,这些反应会生成多官能化产物。特别地,苄基氯化锌与芳基氯化物、溴化物和对甲苯磺酸酯在[Ni(acac)(2)](acac = 乙酰丙酮)和PPh(3)存在下的交叉偶联反应以良好至优异的产率进行,得到相应的二芳基和杂二芳基甲烷。