2-Aminophenyl-1H-pyrazole as a Removable Directing Group for Copper -Mediated C-H Amidation and Sulfonamidation

被引：58
|
作者：
Lee, Wan-Chen Cindy [1 ]
Shen, Yuning [1 ]
Gutierrez, David A. [1 ]
Li, Jie Jack [1 ]
机构：
[1] Univ San Francisco, Dept Chem, 2130 Fulton St, San Francisco, CA 94117 USA
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 11期
关键词：
N-ARYLATION; AMINATION; HETEROARENES; HETEROCYCLES; DERIVATIVES; INHIBITORS; COMPLEXES; ARENES; SULFONYLATION; REACTIVITY;
D O I：
10.1021/acs.orglett.6b01105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Aminophenyl-1H-pyrazole was discovered as a removable bidentate directing group for copper-mediated aerobic oxidative C(sp(2)-H) bond amidation and sulfonamidation. When Cu(OAc)(2) was employed as the copper source and 1,1,3,3-tetramethylguanidine as an organic base, the reaction, optimally carried out overnight in DMSO at 80 degrees C in open air, produced a variety of amides and sulfonamides in moderate to excellent yields. This directing group has proven to be particularly efficient in C-H sulfonamidation.
引用
收藏
页码：2660 / 2663
页数：4
相关论文
共 50 条
  • [31] Theoretical Study of Mechanism and Selectivity of Copper-Catalyzed C-H Bond Amidation of Indoles
    Santoro, Stefano
    Liao, Rong-Zhen
    Himo, Fahmi
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) : 9246 - 9252
  • [32] Heterogeneous copper-based catalysts for the amidation of activated C-H bonds
    Gava, Riccardo
    Biffis, Andrea
    Tubaro, Cristina
    Zaccheria, Federica
    Ravasio, Nicoletta
    CATALYSIS COMMUNICATIONS, 2013, 40 : 63 - 65
  • [33] Directing group strategies in rhodium-catalyzed C-H amination
    Ma, Jiao-li
    Zhou, Xu-ming
    Chen, Jia-lin
    Shi, Jie-xin
    Cheng, Hui-cheng
    Guo, Peng-hu
    Ji, Hong-bing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (38) : 7554 - 7576
  • [34] Copper-Mediated ortho-Nitration of Arene and Heteroarene C-H Bonds Assisted by an 8-Aminoquinoline Directing Group
    Liu, Jidan
    Zhuang, Shaobo
    Gui, Qingwen
    Chen, Xiang
    Yang, Zhiyong
    Tan, Ze
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (04) : 732 - 738
  • [35] The Direct Rh(III)-Catalyzed C-H Amidation of Aniline Derivatives Using a Pyrimidine Directing Group: The Selective Solvent Controlled Synthesis of 1,2-Diaminobenzenes and Benzimidazoles
    Khake, Shrikant M.
    Chatani, Naoto
    ORGANIC LETTERS, 2020, 22 (09) : 3655 - 3660
  • [36] Copper-mediated C-H trifluoromethylation of quinones
    Ilchenko, Nadia O.
    Janson, Par G.
    Szabo, Kalman J.
    CHEMICAL COMMUNICATIONS, 2013, 49 (59) : 6614 - 6616
  • [37] Recent Progress on Copper-Mediated Directing-Group-Assisted C(sp2)-H Activation
    Shang, Ming
    Sun, Shang-Zheng
    Wang, Hong-Li
    Wang, Ming-Ming
    Dai, Hui-Xiong
    SYNTHESIS-STUTTGART, 2016, 48 (24): : 4381 - 4399
  • [38] Copper-mediated ortho C-H primary amination of anilines
    Cheng, Tai-Jin
    Wang, Xing
    Xu, Hui
    Dai, Hui-Xiong
    TETRAHEDRON LETTERS, 2021, 73
  • [39] Copper-catalyzed/mediated aromatic C-H bond functionalization
    Zhang, Ming
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (04) : 269 - 284
  • [40] Copper-Mediated Direct and Selective C-H Thiolation of Quinazolinones
    Sarkar, Writhabrata
    Mishra, Aniket
    Bhowmik, Arup
    Deb, Indubhusan
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 819 - 822
12345