Visible-light-induced palladium-catalyzed formal [3+3] cyclization of 2-iodophenols and cyclopropenes

被引:0
|
作者
Niu, Yue-Jie [1 ,2 ]
Gao, Shu-Xin [1 ,2 ]
Liu, Xin-Xin [1 ,2 ]
Xin, Hong [1 ,2 ]
Duan, Xin-Hua [1 ,2 ]
Guo, Li-Na [1 ,2 ]
Gao, Pin [1 ,2 ]
Li, Pengfei [1 ,2 ,3 ,4 ]
机构
[1] Xi An Jiao Tong Univ, Sch Chem, Dept Chem, Xian Key Lab Sustainable Energy Mat Chem, Xian 710049, Peoples R China
[2] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Condens, Xian 710049, Peoples R China
[3] Xi An Jiao Tong Univ, Frontier Inst Sci & Technol, Xian 710049, Peoples R China
[4] Xi An Jiao Tong Univ, State Key Lab Mech Behav Mat, Xian 710049, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 21期
基金
中国国家自然科学基金;
关键词
RADICAL-ADDITION; CHROMENES; ANNULATION; ETHERS;
D O I
10.1039/d4qo01400f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-induced palladium-catalyzed formal [3 + 3] cyclization of 2-iodophenols and cyclopropenes is presented. This protocol provides a facile approach for the synthesis of 2,2-disubstituted 2H-chromenes with a quaternary carbon center in moderate to good yields. A catalytic cycle involving an aryl radical addition and an intramolecular palladium-catalyzed C-O coupling is proposed for this transformation. Visible-light-induced palladium-catalyzed formal [3 + 3] cyclization of 2-iodophenols and cyclopropenes for the synthesis of 2,2-disubstituted 2H-chromenes with a quaternary carbon center in moderate to good yields.
引用
收藏
页码:6194 / 6199
页数:6
相关论文
共 50 条
  • [1] Palladium-catalyzed Dehydrogenative [3+3] Aromatization of Propyl Ketones and Allyl Carbonates
    Koike, Kenta
    Ueno, Satoshi
    CHEMISTRY LETTERS, 2022, 51 (04) : 489 - 492
  • [2] Benzenediazonium Tetrafluoroborate-Catalyzed Formal [3+3] Cyclization of 4-Hydroxycoumarins With Propargylicalcohols
    Chen, Rongxiang
    Li, Xingshuo
    Xiao, Jutuan
    Zhu, Mingli
    Sun, Aili
    Wang, Kai-Kai
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (12) : 1924 - 1931
  • [3] Palladium-Catalyzed Oxidative Cyclization for the Synthesis of Indolyl/Pyrrolyl 3-Phosphonates
    Mishra, Aniket
    Deb, Indubhusan
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (14) : 2267 - 2272
  • [4] Synthesis of Tetrasubstituted Furans by Palladium-Catalyzed Decarboxylative [3+2] Cyclization of Propargyl β-Keto Esters
    Yoshida, Masahiro
    Ohno, Shoko
    Shishido, Kozo
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (06) : 1604 - 1607
  • [5] Palladium-Catalyzed Carbonylative Cyclization of Terminal Alkynes and Anilines to 3-Substituted Maleimides
    Xu, Jian-Xing
    Wu, Xiao-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) : 3376 - 3380
  • [6] Palladium-catalyzed intermolecular [4+2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides
    Yan, Fachao
    Liang, Hanbing
    Ai, Bing
    Liang, Wenjing
    Jiao, Luyang
    Yao, Shuzhi
    Zhao, Pingping
    Liu, Qing
    Dong, Yunhui
    Liu, Hui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (10) : 2651 - 2656
  • [7] Iridium(III) Photocatalysis: A Visible-Light-Induced Dearomatizative Tandem [4+2] Cyclization to Furnish Benzindolizidines
    Muehmel, Sandra
    Alpers, Dirk
    Hoffmann, Frank
    Brasholz, Malte
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (35) : 12308 - 12312
  • [8] Palladium-Catalyzed [3+3] Annulation between Diarylamines and ,-Unsaturated Acids through CH Activation: Direct Access to 4-Substituted 2-Quinolinones
    Kancherla, Rajesh
    Naveen, Togati
    Maiti, Debabrata
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (23) : 8360 - 8364
  • [9] Gold-Catalyzed Formal [3+3] and [4+2] Cycloaddition Reactions of Nitrosobenzenes with Alkenylgold Carbenoids
    Pagar, Vinayak Vishnu
    Jadhav, Appaso Mahadev
    Liu, Rai-Shung
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) : 20728 - 20731
  • [10] Visible-Light-Induced C(sp3)-H Oxidative Arylation with Heteroarenes
    Liang, Xing-An
    Niu, Linbin
    Wang, Shengchun
    Liu, Jiamei
    Lei, Aiwen
    ORGANIC LETTERS, 2019, 21 (07) : 2441 - 2444