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ÌâÄ¿£ºPalladium-Catalyzed Nucleophilic Substitution/C¨CH Activation/Aromatization Cascade Reaction: One Approach To Construct 6-Unsubstituted Phenanthridines
doi£º10.1021/acs.joc.5b02145
Á¬½Ó£ºhttps://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02145

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Palladium-Catalyzed Nucleophilic Substitution/C-H Activation/Aromatization Cascade Reaction: One Approach To Construct 6-Unsubstituted Phenanthridines
×÷Õß:Han, WY (Han, Wenyong)[ 1 ] ; Zhou, XJ (Zhou, Xiaojian)[ 1 ] ; Yang, SY (Yang, Siyi)[ 1 ] ; Xiang, GY (Xiang, Guangyan)[ 1 ] ; Cui, BD (Cui, Baodong)[ 1 ] ; Chen, YZ (Chen, Yongzheng)[ 1 ]
JOURNAL OF ORGANIC CHEMISTRY
¾í: 80  ÆÚ: 22  Ò³: 11580-11587
DOI: 10.1021/acs.joc.5b02145
³ö°æÄê: NOV 20 2015
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A facile and practical palladium-catalyzed nucleophilic substitution/CH activation/aromatization cascade reaction has been developed. A range of 6-unsubstituted phenanthridines could be obtained in moderate to good yields (3185%) with readily prepared N-Ms arylamines and commercially available 2-bromobenzyl bromide derivatives as starting materials. The potential application of the protocol was also demonstrated by the expeditious synthesis of the natural alkaloid trisphaeridine.
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KeyWords PlusOLYCYCLIC AROMATIC-HYDROCARBONS; INTRAMOLECULAR DIRECT ARYLATION; TRANSITION-METAL-FREE; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; NITROGEN-HETEROCYCLES; FUSED PHENANTHRIDINES; EXPEDITIOUS SYNTHESIS; COUPLING REACTION; CYCLIZATION
×÷ÕßÐÅÏ¢
ͨѶ×÷ÕßµØÖ·: Han, WY (ͨѶ×÷Õß)
              Zunyi Med Univ, Sch Pharm, Zunyi 563000, Peoples R China.
µØÖ·:
              [ 1 ] Zunyi Med Univ, Sch Pharm, Zunyi 563000, Peoples R China
µç×ÓÓʼþµØÖ·:hanwy@zmc.edu.cn; yzchen@zmc.edu.cn
»ù½ð×ÊÖúÖÂл
»ù½ð×ÊÖú»ú¹¹        ÊÚȨºÅ
Science and Technology Department of Guizhou Province        
2015GZ18284
QKHRCTD-2014-4002
Education Department of Guizhou Province        
QJHRCTDZ-2012-03
New Century Excellent Talent of the Ministry of Education        
NCET-13-1069
²é¿´»ù½ð×ÊÖúÐÅÏ¢   
³ö°æÉÌ
AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Àà±ð / ·ÖÀà
Ñо¿·½Ïò:Chemistry
Web of Science Àà±ð:Chemistry, Organic
ÎÄÏ×ÐÅÏ¢
ÎÄÏ×ÀàÐÍ:Article
ÓïÖÖ:English
Èë²ØºÅ: WOS:000365462600040
PubMed ID: 26513449
ISSN: 0022-3263
ÆÚ¿¯ÐÅÏ¢
Impact Factor (Ó°ÏìÒò×Ó): Journal Citation Reports®
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IDS ºÅ: CX1NJ
Web of Science ºËÐĺϼ¯ÖÐµÄ "ÒýÓõIJο¼ÎÄÏ×": 83
Web of Science ºËÐĺϼ¯ÖÐµÄ "±»ÒýƵ´Î": 0
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2Â¥2016-03-05 15:41:39
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412003280: ½ð±Ò+5, ¡ï¡ï¡ï¡ï¡ï×î¼Ñ´ð°¸, Ëٶȷdz£¿ì£¬Ð»Ð» 2016-03-05 18:31:41
Ðľ²_ÒÀÈ»: LS-EPI+1, ¸ÐлӦÖú 2016-03-05 18:40:46
Accession number:       
20154801620710
        Title:        Palladium-Catalyzed Nucleophilic Substitution/C-H Activation/Aromatization Cascade Reaction: One Approach to Construct 6-Unsubstituted Phenanthridines
        Authors:         Han, Wenyong1 Email author hanwy@zmc.edu.cn; Zhou, Xiaojian1; Yang, Siyi1; Xiang, Guangyan1; Cui, Baodong1; Chen, Yongzheng1 Email author yzchen@zmc.edu.cn
        Author affiliation:        1 School of Pharmacy, Zunyi Medical University, Zunyi, China
        Corresponding author:         Han, Wenyong (hanwy@zmc.edu.cn)
        Source title:        Journal of Organic Chemistry
        Abbreviated source title:        J. Org. Chem.
        Volume:        80
        Issue:        22
        Issue date:        November 20, 2015
        Publication year:        2015
        Pages:        11580-11587
        Language:        English
        ISSN:         00223263
        E-ISSN:         15206904
        CODEN:         JOCEAH
        Document type:        Journal article (JA)
        Publisher:        American Chemical Society
        Abstract:        A facile and practical palladium-catalyzed nucleophilic substitution/C-H activation/aromatization cascade reaction has been developed. A range of 6-unsubstituted phenanthridines could be obtained in moderate to good yields (31-85%) with readily prepared N-Ms arylamines and commercially available 2-bromobenzyl bromide derivatives as starting materials. The potential application of the protocol was also demonstrated by the expeditious synthesis of the natural alkaloid trisphaeridine. © 2015 American Chemical Society.
        Number of references:        83
        Main heading:         Catalysis
        Controlled terms:         Chemical activation
        Uncontrolled terms:         Aryl amines - Cascade reactions - Expeditious synthesis - Nucleophilic substitutions - Palladium-catalyzed
        Classification code:         802.2 Chemical Reactions
        DOI:        10.1021/acs.joc.5b02145
        Database:        Compendex
                Compilation and indexing terms, © 2016 Elsevier Inc.
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