Synthesis of Polysubstituted Naphthalenes by Iron-Catalyzed [2+2+2] Annulation of Grignard Reagents with Alkynes

被引:32
|
作者
Ilies, Laurean [1 ]
Matsumoto, Arimasa [1 ]
Kobayashi, Motoaki [1 ]
Yoshikai, Naohiko [1 ]
Nakamura, Eiichi [1 ]
机构
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
alkynes; annulation; C-H bond activation; iron; naphthalene; SUBSTITUTED NAPHTHALENES; INTERNAL ALKYNES; ORTHO-ARYLATION; ARYL IODIDES; ARYLMAGNESIATION; ANNELATION; ACTIVATION; IMINES; ACENES; ARENE;
D O I
10.1055/s-0032-1317077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron catalyzes the oxidative [2+2+2] annulation of an arylmagnesium compound with two molecules of an internal alkyne via C-H bond activation at 0 degrees C to produce polysubstituted naphthalene.
引用
收藏
页码:2381 / 2384
页数:4
相关论文
共 50 条
  • [21] Iron-Catalyzed Coupling Reactions of Vinylic Chalcogenides with Grignard Reagents
    Silveira, Claudio C.
    Mendes, Samuel R.
    Wolf, Lucas
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (11) : 2138 - 2145
  • [22] Iron-catalyzed coupling of aryl grignard reagents with alkyl halides
    Hedstrom, Anna
    Norrby, Per-Ola
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [23] Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
    Domingo-Legarda, Pablo
    Soler-Yanes, Rita
    Teresa Quiros-Lopez, M.
    Bunuel, Elena
    Cardenas, Diego J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (35) : 4900 - 4904
  • [24] Iron-Catalyzed [2+2+2] Cycloaddition Reactions of Diynes with Oxyphosphaethynes To Construct 2-Phosphaphenol Derivatives
    Nakajima, Kazunari
    Liang, Wenbin
    Nishibayashi, Yoshiaki
    ORGANIC LETTERS, 2016, 18 (19) : 5006 - 5009
  • [25] An Eco-Friendly Route to N-Arylindoles by Iron-Catalyzed [2+2+2] Cycloaddition of Diynes with (Indol-1-yl)alkynes
    Chowdhury, Hrishikesh
    Chatterjee, Nachiketa
    Goswami, Avijit
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (35) : 7735 - 7742
  • [26] Iron-Catalyzed Cross-Coupling Reaction of Aryl Grignard Reagents with bis(2-bromovinyl)benzenes
    Operamolla, Alessandra
    Hassan Omar, Omar
    Babudri, Francesco
    Vitulli, Michele
    Farinola, Gianluca M.
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (07) : 573 - 578
  • [27] Iron-catalyzed 1,6-addition of aryl Grignard reagents to 2,4-dienoates and -dienamides
    Fukuhara, K
    Urabe, H
    TETRAHEDRON LETTERS, 2005, 46 (04) : 603 - 606
  • [28] Iron-catalyzed regio- and stereoselective substitution of 2,4-alkadienyl carboxylates with aryl Grignard reagents
    Miyanaka, Kento
    Harada, Tomona
    Shigeta, Masayuki
    Hata, Takeshi
    Urabe, Hirokazu
    TETRAHEDRON LETTERS, 2023, 133
  • [29] Iron-catalyzed highly regio- and stereoselective conjugate addition of 2,3-allenoates with Grignard reagents
    Lu, Zhan
    Chai, Guobi
    Ma, Shengming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) : 14546 - +
  • [30] Synthesis of substituted quinolines by iron-catalyzed coupling reactions between chloroenynes and Grignard reagents
    Seck, M
    Franck, X
    Hocquemiller, R
    Figadère, B
    Peyrat, JF
    Provot, O
    Brion, JD
    Alami, M
    TETRAHEDRON LETTERS, 2004, 45 (09) : 1881 - 1884