β-Selective C-H Arylation of Electron-Deficient Thiophenes, Pyrroles, and Furans

被引:10
|
作者
Liu, Luo-Yan [1 ]
Qiao, Jennifer X. [2 ]
Ewing, William R. [2 ]
Yeung, Kap-Sun [3 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst TSRI, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb, Discovery Chem, POB 4000, Princeton, NJ 08543 USA
[3] Bristol Myers Squibb Res & Dev, Discovery Chem, 100 Binney St, Cambridge, MA 02142 USA
关键词
Thiophene; pyrrole; furan; palladium; arylation; ARYLBORONIC ACIDS; BOND ARYLATION; FUNCTIONALIZATION; ANILINES; CATALYST;
D O I
10.1002/ijch.201900134
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general beta-C-H arylation of electron-deficient thiophenes, pyrroles, and furans has been developed using ligand-modulated palladium catalyst. The use of a modified norbornene is crucial for reversing the conventional alpha-selectivity of these substrates. This method features good yields, high beta-selectivity, and good tolerance of functional groups.
引用
收藏
页码:416 / 418
页数:3
相关论文
共 50 条
  • [1] Direct C-H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids
    Seiple, Ian B.
    Su, Shun
    Rodriguez, Rodrigo A.
    Gianatassio, Ryan
    Fujiwara, Yuta
    Sobel, Adam L.
    Baran, Phil S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13194 - 13196
  • [2] Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents
    Peng, Zhihua
    Yu, Chuanman
    Wang, Yilei
    Wei, Dongyue
    Jiang, Cuiyu
    ORGANOMETALLICS, 2021, 40 (21) : 3678 - 3688
  • [3] Palladium(II)-Catalyzed C-H Bond Arylation of Electron-Deficient Arenes at Room Temperature
    Tredwell, Matthew J.
    Gulias, Moises
    Bremeyer, Nadine Gaunt
    Johansson, Carin C. C.
    Collins, Beatrice S. L.
    Gaunt, Matthew J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1076 - 1079
  • [4] A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes
    Ueda, Kirika
    Yanagisawa, Shuichi
    Yamaguchi, Junichiro
    Itami, Kenichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (47) : 8946 - 8949
  • [5] Site-selective benzylic C-H hydroxylation in electron-deficient azaheterocycles
    Kaur, Milanpreet
    Cooper, Julian C.
    Van Humbeck, Jeffrey F.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (24) : 4888 - 4894
  • [6] Expanding the Scope of Electron-Deficient C-H Building Blocks: Direct Arylation of Pyromellitic Acid Diimide
    Hameury, Sophie
    Kunz, Susanna
    Sommer, Michael
    ACS OMEGA, 2017, 2 (06): : 2483 - 2488
  • [7] Palladium-Catalyzed Desulfitative Direct C-H Arylation of Electron-Deficient Polyfluoroarenes with Sodium Arenesulfinates
    Miao, Tao
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 429 - 436
  • [8] Selective direct C-H polyfluoroarylation of electron-deficient N-heterocyclic compounds
    Li, Shun
    Li, Wen-Jing
    Yang, Xiao
    Sun, Rui
    Tang, Juan
    Zheng, Xue-Li
    Yuan, Mao-Ling
    Li, Rui-Xiang
    Chen, Hua
    Fu, Hai-Yan
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (23): : 3887 - 3895
  • [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] β-Selective C-H Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I
    Ueda, Kirika
    Amaike, Kazuma
    Maceiczyk, Richard M.
    Itami, Kenichiro
    Yamaguchi, Junichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) : 13226 - 13232