Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane
文献类型：期刊论文
| 作者 | Xia, Yuanzhi1,2; Li, Yahong1,2; Li, Wu2 |
| 刊名 | JOURNAL OF ORGANOMETALLIC CHEMISTRY
 |
| 出版日期 | 2008-12-01 |
| 卷号 | 693期号:25页码:3722-3728 |
| 关键词 | Dft Calculation 1 Si-h-b Interaction 2-hydroboration 1 Mechanism 1-organoboration Energy |
| 文献子类 | Article |
| 英文摘要 | The detailed pathway of the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl( vinyl) silane with borane were studied theoretically by DFT calculations. It is found that the 1,2-hydroboration will occur at the C = C moiety when the alkynyl end is substituted, and give the anti-Markovnikov adduct as a result of steric hindrance. From the 1,2-hydroboration intermediate, the intramolecular 1,1-organoboration is a concerted asynchronous process, in which the, C-Si cleavage precedes 1,2-alkyl migration, with activation energy about 25 kcal/mol. Calculations reveal the electronic property of the substituent at the alkyne end has quite limited effect on the 1,1-organoboration activation energy. The ring constrain is found to influence the weak Si-H-B interactions in the 1-silacyclopent-2-ene product most, and similar C-H-B interactions were predicted for the corresponding carbon analogues. (C) 2008 Elsevier B. V. All rights reserved. |
| WOS关键词 | H-B BRIDGES ; RHODIUM-CATALYZED HYDROBORATION ; STEREOSELECTIVE-SYNTHESIS ; SELECTIVE HYDROBORATION ; MARKOVNIKOV HYDROBORATION ; ASYMMETRIC HYDROBORATION ; REDUCTIVE ALKYLATION ; TERMINAL ALKENES ; VINYLSILANES ; OXIDATION |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000260758100007 |
| 源URL | [http://ir.isl.ac.cn/handle/363002/5833]  |
| 专题 | 青海盐湖研究所_青海盐湖研究所知识仓储 中国科学院青海盐湖研究所 |
| 作者单位 | 1.Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China 2.Chinese Acad Sci, Qinghai Inst Salt Lakes, Xining 810008, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xia, Yuanzhi,Li, Yahong,Li, Wu. Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY,2008,693(25):3722-3728. |
| APA | Xia, Yuanzhi,Li, Yahong,&Li, Wu.(2008).Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane.JOURNAL OF ORGANOMETALLIC CHEMISTRY,693(25),3722-3728. |
| MLA | Xia, Yuanzhi,et al."Theoretical study on the consecutive 1,2-hydroboration and 1,1-organoboration reactions of alkyn-1-yl(vinyl) silane with borane".JOURNAL OF ORGANOMETALLIC CHEMISTRY 693.25(2008):3722-3728. |
入库方式： OAI收割
来源：青海盐湖研究所
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