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
  • [11] Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji-Trost Reaction
    Wang, Kang
    Ping, Yifan
    Chang, Taiwei
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13140 - 13144
  • [12] Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes
    Zheng, Baihui
    Li, Xiaotong
    Song, Yang
    Meng, Shuyang
    Li, Yifei
    Liu, Qun
    Pan, Ling
    ORGANIC LETTERS, 2021, 23 (09) : 3453 - 3459
  • [13] Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes
    Zhu, Jia-Liang
    Wu, Sih-Ting
    Shie, Jr-Yun
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) : 3623 - 3633
  • [14] Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs
    Huang, Ke-Xin
    Xie, Ming-Sheng
    Wang, Dong-Chao
    Sang, Ji-Wei
    Qu, Gui-Rong
    Guo, Hai-Ming
    CHEMICAL COMMUNICATIONS, 2019, 55 (90) : 13550 - 13553
  • [15] Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes
    Fang, Songjia
    Jiang, Huanfeng
    Wu, Wanqing
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (02): : 181 - 187
  • [16] Efficient synthesis of 2-amino-3-methylenephthalimides by a palladium-catalyzed intramolecular aminocarbonylation
    Pan, Guoshuai
    Yuan, Yumeng
    Su, Lv
    Zhang, Xiaofeng
    Huang, Qiufeng
    SYNTHETIC COMMUNICATIONS, 2020, 50 (12) : 1892 - 1898
  • [17] Mechanistic insight of TiCl4 catalyzed formal [3+3] cyclization of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles
    Nisa, Riffat Un
    Maria
    Wasim, Fatima
    Mahmood, Tariq
    Ludwig, Ralf
    Ayub, Khurshid
    RSC Advances, 2015, 5 (114): : 94304 - 94314
  • [18] Diastereoselective Construction of 7-Methylenebicyclo[3.2.1]oct-3-en-2-one Derivatives by Palladium-Catalyzed Cyclization of Propargylic Acetates with 2-Oxocyclohex-3-enecarboxylates
    Yoshida, Masahiro
    Sugimura, Chiyuki
    Shishido, Kozo
    ORGANIC LETTERS, 2011, 13 (13) : 3482 - 3485
  • [19] Highly Chemo- and Diastereoselective Construction of Quaternary Stereocenters through Palladium-Catalyzed [3+2] Cyclization of 5-Alkenyl Thiazolones
    Liu, Yue
    Huang, Qian-Wei
    Li, Qing-Zhu
    Leng, Hai-Jun
    Dai, Qing-Song
    Zeng, Rong
    Liu, Yan-Qing
    Zhang, Xiang
    Han, Bo
    Li, Jun-Long
    ORGANIC LETTERS, 2019, 21 (18) : 7478 - 7483
  • [20] Visible-Light-Induced C(sp2)-C(sp3) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins
    Zhang, Ke
    Qiao, Li
    Xie, Jianwei
    Lin, Zhenwei
    Li, Hanjie
    Lu, Ping
    Wang, Yanguang
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14) : 9552 - 9562
12345