Iridium-catalyzed reaction of aroyl chlorides with internal alkynes to produce substituted naphthalenes and anthracenes

被引:97
|
作者
Yasukawa, T [1 ]
Satoh, T [1 ]
Miura, M [1 ]
Nomura, M [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ja0280269
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Benzoyl chlorides efficiently react with 2 equiv of dialkylacetylenes as well as diphenylacetylene in the presence of an iridium catalyst accompanied by decarbonylation to produce 1,2,3,4-tetrasubstituted naphthalenes in good yields. Use of 2-naphthoyl chlorides selectively affords the corresponding anthracene derivatives. Copyright © 2002 American Chemical Society.
引用
收藏
页码:12680 / 12681
页数:2
相关论文
共 50 条
  • [1] Iridium-Catalyzed Addition of Aroyl Chlorides and Aliphatic Acid Chlorides to Terminal Alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 1268 - 1274
  • [2] Iridium-Catalyzed Annulation of N-Arylcarbamoyl Chlorides with Internal Alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (28) : 9602 - 9603
  • [3] Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (19) : 6668 - +
  • [4] Iridium-catalyzed addition of acid chlorides to terminal alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    Journal of the American Chemical Society, 2009, 131 (19): : 6668 - 6669
  • [5] Iridium-catalyzed addition of methanol to internal alkynes
    Konkol, Marcin
    Schmidt, Harry
    Steinborn, Dirk
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 261 (02) : 301 - 305
  • [6] Rhodium-catalyzed reaction of aroyl chlorides with alkynes
    Kokubo, K
    Matsumasa, K
    Miura, M
    Nomura, M
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20): : 6941 - 6946
  • [7] Iron-catalyzed annulation reaction of arylindium reagents and alkynes to produce substituted naphthalenes
    Adak, Laksmikanta
    Yoshikai, Naohiko
    TETRAHEDRON, 2012, 68 (26) : 5167 - 5171
  • [8] Iridium-catalyzed hydroiodination of functionalized alkynes
    Ez-Zoubir, Mehdi
    Brown, Jack A.
    Ratovelomanana-Vidal, Virginie
    Michelet, Veronique
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 433 - 441
  • [9] Electrooxidative Iridium-Catalyzed Regioselective Annulation of Benzoic Acids with Internal Alkynes
    Yang, Qi-Liang
    Jia, Hong-Wei
    Liu, Ying
    Xing, Yi-Kang
    Ma, Rui-Cong
    Wang, Man-Man
    Qu, Gui-Rong
    Mei, Tian-Sheng
    Guo, Hai-Ming
    ORGANIC LETTERS, 2021, 23 (04) : 1209 - 1215
  • [10] Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes
    Huang, QH
    Larock, RC
    ORGANIC LETTERS, 2002, 4 (15) : 2505 - 2508