Pd-Catalyzed Regioselective Direct Double C-H Arylation of 6,7-Benzindoles

被引:8
|
作者
Li, Ping-Gui [1 ,2 ]
Yang, Youqing [1 ]
Zhu, Shuai [2 ]
Li, Hong-Xi [2 ]
Zou, Liang-Hua [2 ]
机构
[1] Nanjing Univ, State Key Lab Coordinat Chem & Chem Engn, Xianlin Ave 163, Nanjing 210093, Jiangsu, Peoples R China
[2] Jiangnan Univ, Sch Pharmaceut Sci, Lihu Ave 1800, Wuxi 214122, Peoples R China
关键词
6,7-Benzindole; Diarylation; C-C coupling; C-H activation; Palladium; N-PIVALOYLINDOLES; INDOLES; FUNCTIONALIZATION; MILD; FORMYLATION; OLEFINATION; ACTIVATION; ALKYLATION; CYANATION; ACCESS;
D O I
10.1002/ejoc.201801473
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed protocol for the first direct diarylation of 6,7-benzindoles with aryl iodides at the C4 and C5 positions was developed. The key to this strategy was the employment of pivaloyl as the directing group at the C3 position and the blocking effect at the C6 and C7 positions. The reaction proceeded very well, providing a series of diarylated 6,7-benzindoles without prefunctionalization at the reactive sites. Several examples on the unexpected monoarylation of 6,7-benzindoles at the C5 position were also presented.
引用
收藏
页码:73 / 76
页数:4
相关论文
共 50 条
  • [1] Pd-Catalyzed Denitrative Intramolecular C-H Arylation
    Asahara, Kitty K.
    Okita, Toshimasa
    Saito, Ami N.
    Muto, Kei
    Nakao, Yoshiaki
    Yamaguchi, Junichiro
    ORGANIC LETTERS, 2019, 21 (12) : 4721 - 4724
  • [2] Pd-Catalyzed β-Selective Direct C-H Bond Arylation of Thiophenes with Aryltrimethylsilanes
    Funaki, Kenji
    Sato, Tetsuo
    Oi, Shuichi
    ORGANIC LETTERS, 2012, 14 (24) : 6186 - 6189
  • [3] Ligand Combination Approach in Pd-Catalyzed Direct C-H Arylation of Benzothiazole and Benzoxazole
    Bakare, Sneha Prasad
    Patil, Mahendra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (02)
  • [4] Pd-Catalyzed Arylation/Oxidation of Benzylic C-H Bond
    Xie, Yongju
    Yang, Yuzhu
    Huang, Lehao
    Zhang, Xunbin
    Zhang, Yuhong
    ORGANIC LETTERS, 2012, 14 (05) : 1238 - 1241
  • [5] Pd-Catalyzed direct C-H arylation of pyrrolo[1,2-a]quinoxalines
    Hao, Di
    Yang, Zhen
    Liu, Yali
    Li, Yang
    Li, Chuntian
    Gu, Yanlong
    Vaccaro, Luigi
    Liu, Jichang
    Liu, Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (04) : 847 - 851
  • [6] Investigation of Pd-catalyzed direct C-H arylation with silole-thiophene system
    Liu, Chuangjun
    Bisen, Milind
    Scott, Colleen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones
    Dabiri, Minoo
    Lehi, Noushin Farajinia
    Movahed, Siyavash Kazemi
    Khavasi, Hamid Reza
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) : 6264 - 6268
  • [8] Pd-catalyzed arylation of Sp3 C-H bonds
    Daugulis, Olafs
    Khan, Rana Kashif M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 132 - 132
  • [9] Pd-Catalyzed β-Selective C-H Arylation of Thiophenes with Triarylantimony Difluorides
    Kitamura, Yuki
    Murata, Yuki
    Oguri, Ayaka
    Matsumura, Mio
    Kakusawa, Naoki
    Naka, Hiroshi
    Yasuike, Shuji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (01) : 138 - 143
  • [10] Pd-Catalyzed Regioselective Decarboxylative/C-H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers
    Rouchet, Jean-Baptiste E. Y.
    Hachem, Mahmoud
    Schneider, Cedric
    Hoarau, Christophe
    ACS CATALYSIS, 2017, 7 (08): : 5363 - 5369