TfOH- and HBF4-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes
文献类型：期刊论文
| 作者 | Xiang, Yu; Li, Zining; Wang, Lu-Ning; Yu, Zhi-Xiang |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2018-08-03 |
| 卷号 | 83期号:15页码:7633-7647 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.8b00393 |
| 英文摘要 | A metal-free, TfOH (1.1 equiv)-mediated formal cycloisomerization of easily prepared allene-alkynylbenzenes to give pyrrolidines and cyclopentanes derivatives was developed. This reaction is initiated by the generation of allylic cation from allene, followed by alkyne's reaction with the allylic cation, to give a vinyl cation, which is finally intercepted by the triflate (TfO) anion. This cycloisomerization can be further tuned to become an acid-mediated intramolecular formal [4+3] cycloaddition by using 10 equiv of TfOH (The excess acid was used to promote the Friedel-Crafts reaction of the acid mediated cycloisomerization products). The present system can also be applied to synthesized F-incorporated products by using HBF4 or Me3OBF4 as the fluoro source. |
| 语种 | 英语 |
| WOS记录号 | WOS:000441112900008 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/42425]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Yu, Zhi-Xiang |
| 作者单位 | Peking Univ, Coll Chem, BNLMS, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xiang, Yu,Li, Zining,Wang, Lu-Ning,et al. TfOH- and HBF4-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(15):7633-7647. |
| APA | Xiang, Yu,Li, Zining,Wang, Lu-Ning,&Yu, Zhi-Xiang.(2018).TfOH- and HBF4-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes.JOURNAL OF ORGANIC CHEMISTRY,83(15),7633-7647. |
| MLA | Xiang, Yu,et al."TfOH- and HBF4-Mediated Formal Cycloisomerizations and [4+3] Cycloadditions of Allene-alkynylbenzenes".JOURNAL OF ORGANIC CHEMISTRY 83.15(2018):7633-7647. |
入库方式： OAI收割
来源：化学研究所
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