DICP OpenIR
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
KeywordCyclization Enones Halogenation Iron Synthetic Methods
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
2010
DOI10.1002/chem.201000686
Volume16Issue:30Pages:9264-9272
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordC-H BOND ; ONE-POT SYNTHESIS ; PRINS-CYCLIZATION ; INTRAMOLECULAR CARBOCYCLIZATION ; ALPHA,BETA-UNSATURATED KETONES ; COUPLING REACTIONS ; CYCLIC ENONES ; ARYL IODIDES ; IRON ; CATALYSIS
AbstractFeCl(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.
Language英语
WOS IDWOS:000281312800039
Citation statistics
Cited Times:31[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/142134
Collection中国科学院大连化学物理研究所
Affiliation1.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
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.
Files in This Item:
There are no files associated with this item.
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Xu, Tongyu]'s Articles
[Yang, Qin]'s Articles
[Li, Dongpo]'s Articles
Baidu academic
Similar articles in Baidu academic
[Xu, Tongyu]'s Articles
[Yang, Qin]'s Articles
[Li, Dongpo]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Xu, Tongyu]'s Articles
[Yang, Qin]'s Articles
[Li, Dongpo]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.