Tunable Di- and Mono-γ-C-H Arylation of Phenylacetamides by Palladium-Catalyzed Domino Reactions

被引:22
|
作者
Liu, Yunyun [1 ]
Huang, Bin [1 ]
Cao, Xiaoji [2 ]
Wan, Jie-Ping [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Zhejiang Univ Technol, Res Ctr Anal & Measurement, 18 Chaowang Rd, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H activation; domino reactions; molecular diversity; step economy; tunable selectivity; STEP-ECONOMICAL SYNTHESIS; DIRECTING GROUP; BOND FUNCTIONALIZATIONS; ARYL HALIDES; METAL; ACTIVATION; 8-AMINOQUINOLINE; SULFENYLATION; CONSTRUCTION; OLEFINATION;
D O I
10.1002/cctc.201600039
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The Pd-catalyzed C-H arylation of phenylacetamides in the position was realized for the first time by means of a domino process consisting of insitu directing group installation and C-H arylation. Unprecedented tunable selectivity between di- and monoactivation of the two identical -C-H bonds was achieved by modifying the reaction conditions; this is a distinct feature of this one-pot procedure for the C-H-activation-based synthesis of diverse amides.
引用
收藏
页码:1470 / 1473
页数:4
相关论文
共 50 条
  • [31] Palladium-Catalyzed Direct C-H Arylation of Cyclic Enaminones with Aryl Iodides
    Yu, Yi-Yun
    Bi, Lei
    Georg, Gunda I.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 6163 - 6169
  • [32] Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides
    Gao, Ke
    Yamamoto, Keita
    Nogi, Keisuke
    Yorimitsu, Hideki
    SYNLETT, 2017, 28 (20) : 2956 - 2960
  • [33] Palladium-catalyzed direct C-H arylation of unactivated arenes with aryl Halides
    Hong, WenKun
    Qiu, Yatao
    Yao, Zhiyi
    Wang, Zhaoyang
    Jiang, Sheng
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4916 - 4919
  • [34] Palladium-Catalyzed C-H Arylation of 2,5-Substituted Pyrroles
    Wagner, Anna M.
    Sanford, Melanie S.
    ORGANIC LETTERS, 2011, 13 (02) : 288 - 291
  • [35] Total synthesis of hebispeptin A and B via palladium-catalyzed C-H arylation
    Chen, Gong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [36] Synthesis of helicenes utilizing palladium-catalyzed double C-H arylation reaction
    Kamikawa, Ken
    Takemoto, Ippei
    Takemoto, Shin
    Matsuzaka, Hiroyuki
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7406 - 7408
  • [37] Palladium-catalyzed aerobic oxidative allylic C-H arylation of alkenes with polyfluorobenzenes
    Jiang, Huanfeng
    Yang, Wanfei
    Chen, Huoji
    Li, Jianxiao
    Wu, Wanqing
    CHEMICAL COMMUNICATIONS, 2014, 50 (54) : 7202 - 7204
  • [38] Palladium-Catalyzed Direct C-H Arylation of Isoxazoles at the 5-Position
    Shigenobu, Masashi
    Takenaka, Kazuhiro
    Sasai, Hiroaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) : 9572 - 9576
  • [39] Palladium-Catalyzed C-H Arylation of 1,2,3-Triazoles
    Zhang, Chengwei
    You, Lin
    Chen, Chuo
    MOLECULES, 2016, 21 (10)
  • [40] Synthesis of Functionalized Spiroindolines via Palladium-Catalyzed Methine C-H Arylation
    Saget, Tanguy
    Perez, David
    Cramer, Nicolai
    ORGANIC LETTERS, 2013, 15 (06) : 1354 - 1357