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
来源：
CHEMCATCHEM | 2016年 / 8卷 / 08期
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
  • [41] Palladium-catalyzed Direct C-H Bond Arylation of Simple Arenes with Aryltrimethylsilanes
    Funaki, Kenji
    Kawai, Hiroshi
    Sato, Tetsuo
    Oi, Shuichi
    CHEMISTRY LETTERS, 2011, 40 (09) : 1050 - 1052
  • [42] Intramolecular Palladium-Catalyzed Alkane C-H Arylation from Aryl Chlorides
    Rousseaux, Sophie
    Davi, Michael
    Sofack-Kreutzer, Julien
    Pierre, Cathleen
    Kefalidis, Christos E.
    Clot, Eric
    Fagnou, Keith
    Baudoin, Olivier
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10706 - 10716
  • [43] Palladium-Catalyzed Direct C-H Arylation of 3-(Methylsulfinyl)thiophenes
    Jiang, Hui
    Bellomo, Ana
    Zhang, Mengnan
    Carroll, Patrick J.
    Manor, Brian C.
    Jia, Tiezheng
    Walsh, Patrick J.
    ORGANIC LETTERS, 2018, 20 (09) : 2522 - 2525
  • [44] Cu-catalyzed controllable C-H mono-/di-/triarylations of imidazolium salts for ionic functional materials
    Li, Shiqing
    Tang, Junbin
    Zhao, Yinsong
    Jiang, Ruyong
    Wang, Tianbao
    Gao, Ge
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2017, 53 (24) : 3489 - 3492
  • [45] Exploration of Aryl Phosphates in Palladium-Catalyzed Mono-α-arylation of Aryl and Heteroaryl Ketones
    Chen, Xiangmeng
    Chen, Zicong
    So, Chau Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6337 - 6346
  • [46] Palladium-catalyzed direct mono-α-arylation of α-fluoroketones with aryl halides or phenyl triflate
    Zhou, Jun
    Fang, Xiang
    Shao, Tongle
    Yang, Xueyan
    Wu, Fanhong
    JOURNAL OF FLUORINE CHEMISTRY, 2016, 191 : 54 - 62
  • [47] PALLADIUM-CATALYZED ARYLATION AT C-H AND C-C BONDS OF MASKED THIAZOLE DERIVATIVES
    Furukawa, Hirotoshi
    Matsumura, Suguru
    Sugie, Atsushi
    Monguchi, Daiki
    Mori, Atsunori
    HETEROCYCLES, 2009, 79 : 303 - 309
  • [48] Palladium-Catalyzed C-H Arylation/Arene Dearomatization Domino Reaction: Expeditious Access to Spiro[4,5]fluorenes
    Han, Lingbo
    Wei, Xin
    Yuan, Yi
    Bai, Lu
    Wang, Hui
    Luan, Xinjun
    ORGANIC LETTERS, 2023, 25 (30) : 5619 - 5623
  • [49] Synthesis of 6-(Trifluoromethyl)phenanthridines via Palladium-Catalyzed Tandem Suzuki/C-H Arylation Reactions
    Wang, Wen-Ying
    Feng, Xia
    Hu, Bo-Lun
    Deng, Chen-Liang
    Zhang, Xing-Guo
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 6025 - 6030
  • [50] Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation
    Li, Bi-Jie
    Yang, Shang-Dong
    Shi, Zhang-Jie
    SYNLETT, 2008, (07) : 949 - 957
12345