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题名: Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies
作者: Xu, Tongyu1;  Yang, Qin1;  Li, Dongpo2;  Dong, Jinhua2;  Yu, Zhengkun1, 3;  Li, Yuxue3
关键词: cyclization ;  enones ;  halogenation ;  iron ;  synthetic methods
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2010
DOI: 10.1002/chem.201000686
卷: 16, 期:30, 页:9264-9272
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
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.
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
语种: 英语
WOS记录号: WOS:000281312800039
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/142057
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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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

Recommended Citation:
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.
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