[4+2] Annulation Cascades of 2-Bromo-1-arylpropan-1-ones with Terminal Alkynes Involving C-Br/C-H Functionalization

被引:14
|
作者
Ouyang, Xuan-Hui [1 ]
Hu, Chao [1 ]
Song, Ren-Jie [1 ]
Li, Jin-Heng [1 ,2 ]
机构
[1] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
关键词
HECK-TYPE REACTION; VISIBLE-LIGHT; RADICAL ALKENYLATION; METALLAPHOTOREDOX CATALYSIS; TANDEM CYCLIZATION; BROMIDES; ALKENES; HALIDES; CARBOCYCLIZATION; DERIVATIVES;
D O I
10.1021/acs.orglett.8b01962
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Straightforward access to various substituted naphthalenones by copper-catalyzed [4 + 2] annulation cascades of 2-bromo-l-arylpropan-1-ones with terminal alkynes is presented. Employing a Cu(MeCN)(4)PF4 catalyst and 1,10-phenanthroline (1,10-Phen) ligand enables the formation of three new C-C bonds in a single reaction via [4 + 2] annulation of a 2-bromo-1-arylpropan-1-one with an alkyne followed by alpha-alkylation with the other 2-bromo-1-arylpropan-1-one with excellent functional group tolerance and step efficiency.
引用
收藏
页码:4659 / 4662
页数:4
相关论文
共 50 条
  • [1] Copper-catalyzed oxidative [2+2+1] annulation of 1,n-enynes with α-carbonyl alkyl bromides through C-Br/C-H functionalization
    Hu, Ming
    Song, Ren-Jie
    Ouyang, Xuan-Hui
    Tan, Fang-Lin
    Wei, Wen-Ting
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2016, 52 (16) : 3328 - 3331
  • [2] Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization
    Tang, Qiuzheng
    Xia, Dexin
    Jin, Xiqing
    Zhang, Qing
    Sun, Xiao-Qiang
    Wang, Congyang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) : 4628 - 4631
  • [3] Site-selective decarbonylative [4+2] annulation of carboxylic acids with terminal alkynes by C-C/C-H activation strategy and cluster catalysis
    Cen, Mengjie
    Ma, Xinyue
    Yang, Xi
    Zhang, Shangshang
    Liu, Long
    Szostak, Michal
    Chen, Tieqiao
    CHEMICAL SCIENCE, 2024, 15 (48) : 20346 - 20354
  • [4] Cobalt(II)-Catalyzed [4+2] Annulation of Picolinamides with Alkynes via C-H Bond Activation
    Yao, Yongqi
    Lin, Qifu
    Yang, Wen
    Yang, Weitao
    Gu, Fenglong
    Guo, Wei
    Yang, Dingqiao
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (25) : 5607 - 5610
  • [5] Annulation Cascades of N-Allyl-N-((2-bromoaryl)ethynyl)amides Involving C-H Functionalization
    Su, Rongkui
    Yang, Xu-Heng
    Hu, Ming
    Wang, Qiu-An
    Li, Jin-Heng
    ORGANIC LETTERS, 2019, 21 (08) : 2786 - 2789
  • [6] Asymmetric Alkenyl C-H Functionalization by CpxRhIII forms 2H-Pyrrol-2-ones through [4+1]-Annulation of Acryl Amides and Allenes
    Wang, Shou-Guo
    Liu, Yang
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (50) : 18136 - 18140
  • [7] Rh(iii)-Catalyzed regioselective C-H [4+2] C-annulation of vinyl enaminones with alkynes to form polysubstituted salicylaldehydes
    Zhao, Yinsong
    Zheng, Qinze
    Yu, Chuangui
    Liu, Zheng
    Wang, Deping
    You, Jingsong
    Gao, Ge
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (19): : 2875 - 2879
  • [8] Tandem Rh-Catalyzed [4+2] Vinylic C-H O-Annulation of Exocyclic Enones with Alkynes and 1,5-H Shift
    Zhao, Yinsong
    Yu, Chuangui
    Wang, Tianbao
    She, Zhijie
    Zheng, Xuesong
    You, Jingsong
    Gao, Ge
    ORGANIC LETTERS, 2018, 20 (04) : 1074 - 1077
  • [9] Ruthenium(II)-Catalyzed C-H/C-H (4+2) Annulation of 2-Aryl-N-heterocycles with Vinylene Carbonate
    Nipate, Dhananjay S.
    Swami, Prakash N.
    Gadekar, Amol B.
    Jangir, Tarun
    Rangan, Krishnan
    Kumar, Anil
    CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (03)
  • [10] Ruthenium-Catalyzed C-H [4+2] Annulation of Quinazolinones with Vinylene Carbonate
    Nan, Jiang
    Huang, Guanjie
    Hu, Yan
    Wang, Bo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (04) : 1537 - 1549