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
  • [31] Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition
    de Nanteuil, Florian
    Waser, Jerome
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (34) : 9009 - 9013
  • [32] Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes
    Huang, QH
    Larock, RC
    ORGANIC LETTERS, 2002, 4 (15) : 2505 - 2508
  • [33] Efficient regioselective approach for polysubstituted benzene derivatives by intermolecular [2+2+2] cyclotrimerization of alkynes
    Wang, Yao-I.
    Hsu, Wei-Lun
    Ho, Feng-Cheng
    Li, Chia-Pei
    Wang, Chaun-Fu
    Chen, Hsiu-Hui
    TETRAHEDRON, 2017, 73 (51) : 7210 - 7216
  • [34] Rhodium-Catalyzed [2+2+2] Cyclotrimerizations of Yndiamides with Alkynes
    Smith, Philip J.
    Tong, Zixuan
    Ragus, Julia
    Solon, Pearse
    Shimkin, Kirk W.
    Anderson, Edward A.
    ORGANIC LETTERS, 2022, 24 (41) : 7522 - 7526
  • [35] Mechanistic Study of the Manganese-Catalyzed [2+2+2] Annulation of 1,3-Dicarbonyl Compounds and Terminal Alkynes
    Yoshikai, Naohiko
    Zhang, Song-Lin
    Yamagata, Ken-ichi
    Tsuji, Hayato
    Nakamura, Eiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 4099 - 4109
  • [36] Ni-Catalyzed Reductive Arylalkenylation of Alkynes for the Selective Synthesis of Polysubstituted Naphthalenes
    Zeng, Meng-Qiang
    Feng, Ke-Xin
    Hu, Bo-Lun
    Tu, Hai-Yong
    Zhang, Xing-Guo
    ORGANIC LETTERS, 2022, 24 (29) : 5386 - 5390
  • [37] Iron-catalyzed stereospecific arylation of enol tosylates using Grignard reagents
    Wei, Yi-Ming
    Ma, Xiao-Di
    Wang, Lei
    Duan, Xin-Fang
    CHEMICAL COMMUNICATIONS, 2020, 56 (07) : 1101 - 1104
  • [38] Iron-catalyzed cross-coupling of imidoyl chlorides with Grignard reagents
    Ottesen, LK
    Ek, F
    Olsson, R
    ORGANIC LETTERS, 2006, 8 (09) : 1771 - 1773
  • [39] Iron-catalyzed cross-coupling of alkenyl sulfides with Grignard reagents
    Itami, K
    Higashi, S
    Mineno, M
    Yoshida, J
    ORGANIC LETTERS, 2005, 7 (07) : 1219 - 1222
  • [40] Iron-Catalyzed, Directed Oxidative Arylation of Olefins with Organozinc and Grignard Reagents
    Ilies, Laurean
    Okabe, Jun
    Yoshikai, Naohiko
    Nakamura, Eiichi
    ORGANIC LETTERS, 2010, 12 (12) : 2838 - 2840