Palladium-Catalyzed Cascade Cyclization and Alkynylation of 2-Alkynylphenols with Bromoalkynes

被引:0
|
作者
Feng, Yu [1 ]
Zhang, Jiangjie [2 ]
Ying, Jun [2 ]
Lv, Yue [1 ]
Tang, Keqi [1 ]
Luo, Junfei [1 ]
机构
[1] Ningbo Univ, Inst Mass Spectrometry, Sch Mat Sci & Chem Engn, Ningbo 315211, Peoples R China
[2] Zhejiang Sci Tech Univ, Sch Chem & Chem Engn, Hangzhou 310018, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
Palladium; Benzofurans; Cyclization; Alkynylation; 2-Alkynylphenols;
D O I
10.1002/ajoc.202400283
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed cascade cyclization and alkynylation of 2-alkynylphenols with bromoalkynes to the synthesis of 3-alkynylbenzofuran scaffolds has been developed. A variety of 3-alkynylbenzofuran derivatives were prepared in good yields under mild conditions. Notably, this protocol was applied to the late-stage modification of bioactive molecule. A palladium-catalyzed cascade cyclization and alkynylation of 2-alkynylphenols with bromoalkynes has been reported. The method provides an efficient tool to construct the 3-alkynylbenzofuran derivatives, as well as late-stage modifies the bioactive molecule. image
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Cascade Cyclization/Alkynylation Reactions
    Li, Jianxiao
    Yang, Shaorong
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (23) : 4114 - 4128
  • [2] Palladium-Catalyzed Sequential Oxidative Cyclization/Coupling of 2-Alkynylphenols and Alkenes: A Direct Entry into 3-Alkenylbenzofurans
    Martinez, Claudio
    Alvarez, Rosana
    Aurrecoechea, Jose M.
    ORGANIC LETTERS, 2009, 11 (05) : 1083 - 1086
  • [3] Palladium-Catalyzed C2-Selective Alkynylation of Indoles with Bromoalkynes
    Zhao, Shufang
    Ma, Wenchao
    Yasir, Mumtaz
    Zhou, Xinli
    Cheng, Jintang
    Jiang, Chao
    CHEMISTRYSELECT, 2018, 3 (47): : 13319 - 13322
  • [4] Palladium-catalyzed regioselective C-H alkynylation of indoles with bromoalkynes in water
    Wu, Wanqing
    Fang, Songjia
    Jiang, Guangbin
    Li, Meng
    Jiang, Huanfeng
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2200 - 2204
  • [5] Palladium-Catalyzed Cascade Cyclization/Alkynylation and Alkenylation of Alkynone O-Methyloximes with Terminal Alkynes
    Li, Jianxiao
    Hu, Miao
    Li, Chunsheng
    Li, Can
    Li, Jiawei
    Wu, Wanqing
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (14) : 2707 - 2719
  • [6] Palladium-catalyzed alkynylation
    Negishi, E
    Anastasia, L
    CHEMICAL REVIEWS, 2003, 103 (05) : 1979 - 2017
  • [7] Palladium-Catalyzed Cascade Cyclization of Ynamides to Azabicycles
    Greenaway, Rebecca L.
    Campbell, Craig D.
    Holton, Oliver T.
    Russell, C. Adam
    Anderson, Edward A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (51) : 14366 - 14370
  • [8] Palladium-catalyzed decarboxylation of vinyloxazolidine-2,4-diones used in the divergent reaction with 2-alkynylphenols and 2-alkynylanilines
    Yang, Zhong-Lie
    Wang, Zhen-Hua
    Zhang, Yan-Ping
    You, Yong
    Zhao, Jian-Qiang
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025,
  • [9] Assembly of Functionalized 4-Alkynylisoxazoles by Palladium-Catalyzed Three-Component Cascade Cyclization/Alkynylation
    Li, Jianxiao
    Huang, Ruikang
    Li, Can
    Lin, Shao
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (13) : 2309 - 2315
  • [10] Novel and selective palladium-catalyzed annulations of 2-alkynylphenols to form 2-substituted 3-halobenzo[b]furans
    Liang, Yun
    Tang, Shi
    Zhang, Xu-Dong
    Mao, Li-Qiu
    Xie, Ye-Xiang
    Li, Jin-Heng
    ORGANIC LETTERS, 2006, 8 (14) : 3017 - 3020