摘要
以丙炔酸、仲胺、烷基醛和甲醛为试剂,在过渡金属铜催化下高效地构建了一系列非对称1,4-二氨基-2-丁炔化合物.该多组分一锅二步方法历经A3-脱羧偶联生成关键中间体炔丙胺,随后该中间体加成到原位形成的亚胺离子上,最终以中等到优异的产率得到交叉偶联产物.该策略成功地将脂肪族仲胺引入到反应体系中,具有底物胺兼容性较好的特点.
A highly selective and efficient copper-catalyzed sequential approach for the one-pot two-step synthesis of unsymmetrical 1,4-diamino-2-butynes from propiolic acid,secondary alkylamine,aldehyde and formaldehyde solution has been developed.The process of this reaction was involved in the generation of key intermediate propargylamines which were obtained via decarboxylative A3-coupling reaction.After that,the intermediate propargylamines would react with in situ formed iminium ions to give the cross-coupling target products in moderate to excellent yields under microwave irradiation.
作者
刘博瑜
徐仙君
黄立梁
冯煌迪
Liu Boyu;Xu Xianjun;Huang Liliang;Feng Huangdi(College of Chemistry and Chemical Engineering,Shanghai University of Engineering Science,Shanghai 201620)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2020年第5期1290-1296,共7页
Chinese Journal of Organic Chemistry
基金
上海市自然科学基金(No.15ZR1418800)
中国博士后科学基金(No.2016M601681)
上海工程技术大学(Nos.cs1704006,201810856017).
关键词
非对称二氨基丁炔
脱羧偶联
A3-偶联
交叉偶联
铜催化
unsymmetrical diaminobutynes
decarboxylative coupling
A3-coupling
cross-coupling
copper-catalyzed