吲哚基官能化邻碳硼烷的研究  

Study of Indolyl Functionalization of o-Carborane

作　　者：纪娴 易鑫磊 赵志伟 黄泽明 王芬华[1] 张海燕 JI Xian;YI Xinlei;ZHAO Zhiwei;HUANG Zeming;WANG Fenhua;ZHANG Haiyan(School of Chemical and Environmental Engineering,Anhui Polytechnic University,Wuhu 241000,China;General Manager Office,Anhui Kerui Consulting Services Co.,Ltd.,Wuhu 241000,China)

机构地区：[1]安徽工程大学化学与环境工程学院,安徽芜湖241000 [2]安徽科瑞咨询服务有限公司总经办,安徽芜湖241000

出　　处：《安徽工程大学学报》2024年第3期1-7,共7页Journal of Anhui Polytechnic University

基　　金：“洁净催化”安徽省重点实验室开放课题(LCCE-01)。

摘　　要：以炔丙基吲哚为原料,直接与硼烷发生加成反应,即可得到吲哚修饰的邻碳硼烷单C-H键活化衍生物(C_(8)H_(6)NCH_(2))-C_(2)HB_(10)H_(10),经过核磁共振波谱、高分辨质谱、X-射线单晶衍射表征,确定了该化合物的结构。结构表明,该化合物为正交晶系,P 212121空间群。为了进一步拓展底物,在吲哚骨架上进一步衍生。采用曼尼希反应,在吲哚3-位引入四氢吡咯亚甲基,合成了化合物[3-(C_(4)H_(8)NCH_(2))C_(8)H_(5)NCH_(2)]-C_(2)HB_(10)H_(10),该化合物为单斜晶系,C_(2)/c空间群。该合成方法成功地将富电子吲哚基团引入到缺电子碳硼烷骨架中,为发展新型硼簇化合物的合成提供了一种新的方法。A mono C-H bond activation derivative(C_(8)H_(6)NCH_(2))-C_(2)HB_(10)H_(10) was synthesized by the direct addition reaction of propargyl indole with borane.It was characterized by NMR spectroscopy,high resolution mass spectrum and single crystal X-ray diffraction.The structure showed the compound was crystallized in orthorhombic crystal system,P 2_(1)2_(1)2_(1) space group.In order to further expand the application,indole skeleton was modified at 3-position with tetrahydropyrrolyl methylene to synthesize compound[3-(C_(4)H_(8)NCH_(2))C_(8)H_(5)NCH_(2)]-C_(2)HB_(10)H_(10)by Mannich reaction,with the crystal structure in monoclinic crystal system,C_(2)/c space group.This synthetic method succeeded in introducing electron-rich indolyl to electron-deficient carborane skeleton,and provided a new approach for the synthesis of novel boron cluster compounds.

关 键 词：邻碳硼烷 1 3-双取代吲哚 C-H键官能化 合成 

分 类 号：O627.3[理学—有机化学]