氮杂环卡宾和金属配合物共催化构筑高烯丙醇化合物

西安科技大学 化学与化工学院,陕西 西安 710054

氮杂环卡宾催化剂; 金属配合物; 安息香缩合反应; 烯丙基亲核取代反应

Construction of homoallylic alcohol compounds catalyzed by N-heterocyclic carbenes and metal complexes
HE Jin-mei,QU Meng-nan

(College of Chemistry and Chemical Engineering,Xi'an University of Science and Technology,Xi'an 710054,China)

N-heterocyclic carbenes; metal complexe; benzoin condensations; allylic nucleophilic substitution reactions

备注

氮杂环卡宾作为有机催化剂可将醛类化合物反应极性发生翻转,使醛类化合物由亲电性转化为亲核性,通过研究氮杂环卡宾和金属配合物的兼容性,利用二者协同催化的反应体系,以各类芳香醛和烯丙基醋酸酯为起始原料,有效地制备了高烯丙醇化合物。研究结果表明:选择噻唑类氮杂环卡宾催化剂和Pd(OAc)2/PPh3为共催化剂,2倍当量的KOBut作碱,CH2Cl2作溶剂的条件下,可高效地得到高烯丙醇化合物,该反应适用范围较广,可用于制备各类高烯丙醇化合物。

N-heterocyclic carbenes as a kind of versatile organocatalysts was utilized in a variety of transformations. The highly nucleophilic carbenes can react with kinds of aldehydes,resulting umpolung aldehyde or acyl anion equivalents. Based on the characteristic of N-heterocyclic carbenes,metal complexe catalyst was utilized in one pot as co-catalyst to prepare homoallylic alcohol compounds. The result of experiment showed that when thiazolium salt and Pd(OAc)2/ PPh3 were utilized as co-catalyst,2 equivalent of KOBut was used as base,homoallylic alcohol compounds were effectively obtained from various aldehydes and allylic acetates in good yields under the moderate condition.