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DOI | 10.1126/science.aao5923 |
Organocalcium-mediated nucleophilic alkylation of benzene | |
Wilson, Andrew S. S.1; Hill, Michael S.1; Mahon, Mary F.1; Dinoi, Chiara2,3; Maron, Laurent2,3 | |
2017-12-01 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 358期号:6367页码:1168-1171 |
文章类型 | Article |
语种 | 英语 |
国家 | England; France |
英文摘要 | The electrophilic aromatic substitution of a C-H bond of benzene is one of the archetypal transformations of organic chemistry. In contrast, the electron-rich p-system of benzene is highly resistant to reactions with electron-rich and negatively charged organic nucleophiles. Here, we report that this previously insurmountable electronic repulsion may be overcome through the use of sufficiently potent organocalcium nucleophiles. Calcium n-alkyl derivatives-synthesized by reaction of ethene, but-1-ene, and hex-1-ene with a dimeric calcium hydride-react with protio and deutero benzene at 60 degrees C through nucleophilic substitution of an aromatic C-D/H bond. These reactions produce the n-alkyl benzenes with regeneration of the calcium hydride. Density functional theory calculations implicate an unstabilized Meisenheimer complex in the C-H activation transition state. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000416584000037 |
WOS关键词 | SOLUBLE CALCIUM HYDRIDE ; HEAVY GRIGNARD-REAGENTS ; COMPLEXES ; POLYMERIZATION ; SUBSTITUTION ; STRONTIUM ; HYDROGEN ; CLUSTER ; ARENES ; LIGAND |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/197437 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England; 2.Univ Toulouse, 135 Ave Rangueil, F-31077 Toulouse, France; 3.Univ Toulouse III Paul Sabatier, CNRS, Inst Natl Sci Appl, UMR 5215,LPCNO, 135 Ave Rangueil, F-31077 Toulouse, France |
推荐引用方式 GB/T 7714 | Wilson, Andrew S. S.,Hill, Michael S.,Mahon, Mary F.,et al. Organocalcium-mediated nucleophilic alkylation of benzene[J]. SCIENCE,2017,358(6367):1168-1171. |
APA | Wilson, Andrew S. S.,Hill, Michael S.,Mahon, Mary F.,Dinoi, Chiara,&Maron, Laurent.(2017).Organocalcium-mediated nucleophilic alkylation of benzene.SCIENCE,358(6367),1168-1171. |
MLA | Wilson, Andrew S. S.,et al."Organocalcium-mediated nucleophilic alkylation of benzene".SCIENCE 358.6367(2017):1168-1171. |
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