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Iron(III)-Catalyzed Cyclization of Alkynyl Aldehyde Acetals: Experimental and Computational Studies
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
2010
DOI10.1002/chem.201000686
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
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
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.
语种英语
WOS记录号WOS:000281312800039
引用统计
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/142057
专题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
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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.
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