Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies
文献类型：期刊论文
| 作者 | Xu, Tongyu1; Yang, Qin1; Li, Dongpo2; Dong, Jinhua2; Yu, Zhengkun1,3; Li, Yuxue3 |
| 刊名 | chemistry-a european journal
 |
| 出版日期 | 2010 |
| 卷号 | 16期号:30页码:9264-9272 |
| 关键词 | cyclization enones halogenation iron synthetic methods |
| 英文摘要 | fecl(3)center dot 6h(2)o- and febr(3)-catalyzed prins cyclization/halogenation of alkynyl aldehyde acetals has been realized with acetyl chloride or bromide as halogen source in dichloromethane to afford 2-(1-halobenzylidene or alkylidene)-substituted five-membered carbo- and heterocycles, and thus provides an alternative route for vinylic c-cl and c-br bond formation. five- to eight-membered cyclic enones were efficiently synthesized by fecl(3)center dot 6h(2)o-catalyzed intramolecular cyclization of alkynyl aldehyde acetals in acetone under mild conditions. an oxocarbonium species generated in situ is proposed to initiate the reaction, and the target products are formed via vinylogous carbenium cation and oxete intermediates according to dft calculations. intermolecular reactions of alkynes and aldehyde acetals were also investigated with 20-40 mol% fecl(3)center dot 6h(2)o catalyst, and produced alpha,beta-unsaturated enones and chlorinated indene derivatives. the present protocol has applications in the synthesis of carbo-, oxa- and azacycles. |
| WOS标题词 | science & technology ; physical sciences |
| 类目[WOS] | chemistry, multidisciplinary |
| 研究领域[WOS] | chemistry |
| 关键词[WOS] | c-h bond ; one-pot synthesis ; prins-cyclization ; intramolecular carbocyclization ; alpha,beta-unsaturated ketones ; coupling reactions ; cyclic enones ; aryl iodides ; iron ; catalysis |
| 收录类别 | SCI ; IC ; CCR |
| 语种 | 英语 |
| WOS记录号 | WOS:000281312800039 |
| 公开日期 | 2015-11-17 |
| 源URL | [http://159.226.238.44/handle/321008/142134]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 作者单位 | 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China 2.Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Liaoning, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xu, Tongyu,Yang, Qin,Li, Dongpo,et al. Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies[J]. chemistry-a european journal,2010,16(30):9264-9272. |
| APA | Xu, Tongyu,Yang, Qin,Li, Dongpo,Dong, Jinhua,Yu, Zhengkun,&Li, Yuxue.(2010).Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies.chemistry-a european journal,16(30),9264-9272. |
| MLA | Xu, Tongyu,et al."Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies".chemistry-a european journal 16.30(2010):9264-9272. |
入库方式： OAI收割
来源：大连化学物理研究所
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