K2S2O8-Mediated Radical Cascade Alkylation/Cyclization of Ynones: Access to Oxoalkyl-Substituted Indenones

被引:2
作者
Tian, Si-Wei [1 ]
Xiong, Fang-Ting [1 ]
Xiong, Bi-Quan [1 ]
Zhong, Long-Jin [1 ]
Tang, Ke-Wen [1 ]
Liu, Yu [1 ]
机构
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 31期
基金
中国国家自然科学基金;
关键词
oxidative; alkylation; cyclization; indenones; radical; C(sp(3))-H bonds; C-H FUNCTIONALIZATION; CATALYZED ANNULATION; ALKYNES; CYCLIZATION; ALKYLATION; KETONES; ACETONE; ALKANES; DESIGN; BONDS;
D O I
10.1002/slct.202302484
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient oxidative-promoted radical cascade annulation of ynone derivatives with ketones for the construction of a series of oxoalkyl-substituted indenones in moderate to good yields is described. The control experiment results indicate that the oxidative acetmethylation/arylation of ynone derivatives involves a radical cascade cyclization process. This is an operationally simple and efficient protocol which will be attractive in organic synthesis chemistry.
引用
收藏
页数:5
相关论文
共 77 条
  • [1] Indenone derivatives:: A novel template for peroxisome proliferator-activated receptor γ (PPARγ) agonists
    Ahn, Jin Hee
    Shin, Mi Sik
    Jung, Sun Ho
    Kang, Seung Kyu
    Kim, Kwang Rok
    Rhee, Sang Dal
    Jung, Won Hoon
    Yang, Sung Don
    Kim, Seung Jun
    Woo, Joo Rang
    Lee, Jeong Hyung
    Cheon, Hyae Gyeong
    Kim, Sung Soo
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) : 4781 - 4784
  • [2] Acetone-Linked Peptides: A Convergent Approach for Peptide Macrocyclization and Labeling
    Assem, Naila
    Ferreira, David J.
    Wolan, Dennis W.
    Dawson, Philip E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8665 - 8668
  • [3] Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes
    Cai, Tao
    Shen, Fangqi
    Ni, Yuqi
    Xu, Huiting
    Shen, Runpu
    Gao, Yuzhen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 1002 - 1011
  • [4] Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal
    Chen, Shuyou
    Yu, Jintao
    Jiang, Yan
    Chen, Fan
    Cheng, Jiang
    [J]. ORGANIC LETTERS, 2013, 15 (18) : 4754 - 4757
  • [5] Synthesis of 1,4-dithiins and 1,4-diselenins from alkynes and elemental sulfur/selenium under transition metal-free conditions with high regioselectivity
    Cheng, Lu
    Wang, Mengdan
    Gu, Yingge
    He, Peng
    Wang, Zongkang
    Zhuang, Ziyi
    Kong, Lingkai
    Li, Yanzhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11) : 2708 - 2713
  • [6] Palladium-Catalyzed Annulation of Alkynes with Ortho-Halide-Containing Benzyl Alcohols in Aqueous Medium
    Feng, Jie
    Lu, Guoping
    Lv, Meifang
    Cai, Chun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10561 - 10567
  • [7] Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides
    Fu, Wai Chung
    So, Chau Ming
    Chow, Wing Kin
    Yuen, On Ying
    Kwong, Fuk Yee
    [J]. ORGANIC LETTERS, 2015, 17 (18) : 4612 - 4615
  • [8] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations
    Girard, Simon A.
    Knauber, Thomas
    Li, Chao-Jun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 74 - 100
  • [9] Oxidative dual C-H selenation of imidazoheterocycles with ethers or alkanes using selenium powder via a radical pathway
    Guo, Tao
    Wei, Xu-Ning
    Liu, Yu
    Zhang, Pan-Ke
    Zhao, Yun-Hui
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (09): : 1414 - 1422
  • [10] Guidelines for radical reactions: some thirty years on
    Hancock, Amber N.
    Schiesser, Carl H.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (85) : 9892 - 9895