Palladium-Catalyzed Selective Synthesis of 3-Hydroxy-2-oxindoles via Cascade C-H Cycloaddition and Oxidation of -Aminoacetophenones

被引：1
|
作者：
Liao, Yan-Yan [1 ]
Xu, Li [1 ]
Tang, Ri-Yuan [1 ]
Zheng, Wen-Xu [1 ]
机构：
[1] South China Agr Univ, Dept Appl Chem, Coll Mat & Energy, Guangzhou 510642, Guangdong, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 23期
关键词：
palladium; indole; cyclization; oxidation; C-H functionalization; NUCLEOPHILIC-ADDITION; CYCLIZATION REACTIONS; ALPHA-KETOAMIDES; CARBON; 2-OXINDOLES;
D O I：
10.1055/s-0037-1610537
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the synthesis of 3-hydroxy-2-oxindole (3-hydroxyindolin-2-one) derivatives by palladium-catalyzed tandem C-H cycloaddition and oxidation of a-aminoacetophenone has been developed. In the presence of Pd(OAc) 2 and AgOAc, a variety of 3-hydroxy-2oxindoles were synthesized in moderate yields. Control experiments show that the selective cycloaddition occurs prior to the oxidation is crucial for this successful chemical transformation.
引用
收藏
页码：4645 / 4650
页数：6
相关论文
共 50 条
  • [21] Total Synthesis of (±)-Cephanolides B and C via a Palladium-Catalyzed Cascade Cyclization and Late-Stage sp3 C-H Bond Oxidation
    Xu, Lun
    Wang, Chao
    Gao, Ziwei
    Zhao, Yu-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) : 5653 - 5658
  • [22] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [23] Palladium-catalyzed Asymmetric Allylic C-H Oxidation for the Formal Synthesis of Gonytolide C
    Liu, Peng
    Wang, Pu-Sheng
    CHEMISTRY LETTERS, 2017, 46 (08) : 1190 - 1192
  • [24] Efficient Synthesis of 3-Azaarene-substituted 3-Hydroxy-2-oxindoles via Aluminium Chloride Catalyzed sp3-C-H Functionalization
    Zhai, Jiaojiao
    Yao, Zhigang
    Xu, Fan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) : 1639 - 1645
  • [25] Expeditious Synthesis of Tetrasubstituted Helical Alkenes by a Cascade of Palladium-Catalyzed C-H Activations
    Liu, Hongqiang
    El-Salfiti, Mohamed
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9846 - 9850
  • [26] Asymmetric Palladium-Catalyzed C-H Functionalization Cascade for Synthesis of Chiral 3,4-Dihydroisoquinolones
    Sun, Manman
    Wu, Haijian
    Xia, Xiangyu
    Chen, Weida
    Wang, Zhiming
    Yang, Jianguo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 12835 - 12847
  • [27] Palladium-catalyzed C-H functionalization of N-arylpropiolamides with aryliodonium salts:: Selective synthesis of 3-(1-arylmethylene)oxindoles
    Tang, Shi
    Peng, Peng
    Zhong, Ping
    Li, Jin-Heng
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5476 - 5480
  • [28] A simple and sustainable tetrabutylammonium fluoride (TBAF)-catalyzed synthesis of azaarene-substituted 3-hydroxy-2-oxindoles through sp3 C-H functionalization
    Kumari, Kumkum
    Allam, Bharat Kumar
    Singh, Krishna Nand
    RSC ADVANCES, 2014, 4 (38) : 19789 - 19793
  • [29] Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation
    Yang, Yuzhong
    Zhou, Bang
    Zhu, Xiaoming
    Deng, Guobo
    Liang, Yun
    Yang, Yuan
    ORGANIC LETTERS, 2018, 20 (17) : 5402 - 5405
  • [30] Synthesis of Functionalized Spiroindolines via Palladium-Catalyzed Methine C-H Arylation
    Saget, Tanguy
    Perez, David
    Cramer, Nicolai
    ORGANIC LETTERS, 2013, 15 (06) : 1354 - 1357
12345