Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis

被引：41
|
作者：
Shirakawa, Eiji [1 ]
Masui, Seiji [1 ]
Narui, Rintaro [1 ]
Watabe, Ryo [1 ]
Ikeda, Daiji [1 ]
Hayashi, Tamio [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 34期
关键词：
MAGNESIUM MEDIATED CARBOMETALLATION; STEREOSELECTIVE-SYNTHESIS; ACETYLENIC-COMPOUNDS; PROPARGYL ALCOHOLS; DIRECT ROUTES; COMPLEX; ARYLMAGNESIATION; CARBOLITHIATION; REACTIVITY; CARBOSTANNYLATION;
D O I：
10.1039/c1cc11989c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Phenyl- and vinyllithiums having an alkyl substituent at their ortho- and cis-position, respectively, readily added to alkynes in the presence of 5 mol% of Fe(acac)(3). The reaction of o-(trimethylsilyl) phenyllithium with alkynes gave benzosiloles through an addition-cyclization sequence.
引用
收藏
页码：9714 / 9716
页数：3
相关论文
共 50 条
  • [31] Iron-catalyzed regio- and stereoselective carbolithiation of alkynes
    Hojo, M
    Murakami, Y
    Aihara, H
    Sakuragi, R
    Baba, Y
    Hosomi, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (03) : 621 - 623
  • [32] Selective iron-catalyzed transfer hydrogenation of terminal alkynes
    Wienhoefer, Gerrit
    Westerhaus, Felix A.
    Jagadeesh, Rajenahally V.
    Junge, Kathrin
    Junge, Henrik
    Beller, Matthias
    CHEMICAL COMMUNICATIONS, 2012, 48 (40) : 4827 - 4829
  • [33] Iron-catalyzed thioetherification of thiols with aryl iodides
    Wu, Jhih-Ru
    Lin, Che-Hung
    Lee, Chin-Fa
    CHEMICAL COMMUNICATIONS, 2009, (29) : 4450 - 4452
  • [34] Iron-catalyzed alkylations of aryl sulfamates and carbamates
    Silberstein, Amanda L.
    Ramgren, Stephen D.
    Garg, Neil K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [35] Iron-Catalyzed Oxyalkylation of Terminal Alkynes with Alkyl Iodides
    Deng, Weili
    Ye, Changqing
    Li, Yajun
    Li, Daliang
    Bao, Hongli
    ORGANIC LETTERS, 2019, 21 (01) : 261 - 265
  • [36] Practical iron-catalyzed dehalogenation of aryl halides
    Czaplik, Waldemar Maximilian
    Grupe, Sabine
    Mayer, Matthias
    Jacobi von Wangelin, Axel
    CHEMICAL COMMUNICATIONS, 2010, 46 (34) : 6350 - 6352
  • [37] Iron-Catalyzed Alkylations of Aryl Sulfamates and Carbamates
    Silberstein, Amanda L.
    Ramgren, Stephen D.
    Garg, Neil K.
    ORGANIC LETTERS, 2012, 14 (14) : 3796 - 3799
  • [38] Iron-catalyzed synthesis of cinnarizine
    Shakhmaev, R. N.
    Sunagatullina, A. Sh
    Zorin, V. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (01) : 95 - 97
  • [39] Iron-catalyzed synthesis of cinnarizine
    R. N. Shakhmaev
    A. Sh. Sunagatullina
    V. V. Zorin
    Russian Journal of Organic Chemistry, 2015, 51 : 95 - 97
  • [40] Iron-catalyzed synthesis of heterocycles
    Majumdar, Krishna C.
    De, Nirupam
    Ghosh, Tapas
    Roy, Brindaban
    TETRAHEDRON, 2014, 70 (33) : 4827 - 4868
12345