CAJ | 학술논문

构建C-N键,在有机合成中占有非常重要的地位.本文介绍了一种简单、方便的合成芳香族胺化物的方法.在100°C和二甲亚砜溶剂体系中,卤代芳烃分别和伯、仲两类胺在叔丁醇钾催化下经过1h反应,以45%～90%的收率,生成一系列芳香族胺化物.方法进一步拓宽了叔丁醇钾催化的 C-N 交叉偶联反应的底物,并显示出独特的底物选择性,即对富电子卤代芳烃有很好的活性.据推测,本偶联反应是通过先形成苯炔中间体,再与胺发生交叉偶联的历程进行的.
구건C-N건,재유궤합성중점유비상중요적지위.본문개소료일충간단、방편적합성방향족알화물적방법.재100°C화이갑아풍용제체계중,서대방경분별화백、중량류알재숙정순갑최화하경과1h반응,이45%～90%적수솔,생성일계렬방향족알화물.방법진일보탁관료숙정순갑최화적 C-N 교차우련반응적저물,병현시출독특적저물선택성,즉대부전자서대방경유흔호적활성.거추측,본우련반응시통과선형성분결중간체,재여알발생교차우련적역정진행적.
The construction of C-N bond stands at an important position in the area of organic synthesis. In this paper, a simple and efficient procedure has been developed for the synthesis of arylamines. In DMSO at 100 oC, cross-coupling reactions of aryl halides with various amines catalyzed by t-BuOK provide a series of arylamines in the yield of 45%～90%in 1 h. The present procedure not only broadens the precursor compounds suitable for t-BuOK-catalyzed cross-coupling reaction, but also exhibits characteristic chemoselectivity such as being favorable to electron-rich aryl halides. The reaction appears to proceed through in situ formation of a benzyne intermediate, followed by a C-N cross-coupling to arylamine.