SYNTHESES OF FUNCTIONALIZED CYCLIC MOLECULES BY PALLADIUM-CATALYZED CYCLIZATION OF PROPARGYLIC ESTERS WITH BIS-NUCLEOPHILES

被引:25
作者
Yoshida, Masahiro [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
基金
日本学术振兴会;
关键词
Cyclization; Palladium Catalyst; Propargylic Compound; Nucleophile; RING EXPANSION REACTION; CARBONATES; DERIVATIVES; PHENOLS; CONSTRUCTION; CHEMISTRY; OXIRANES; 4-METHOXYCARBONYLOXY-2-BUTYN-1-OLS; SUBSTITUTION; METHODOLOGY;
D O I
10.3987/REV-13-776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is known that propargylic esters react with palladium complex leading to pi-propargylpalladium complexes, which further cause various transformations in the presence of soft nucleophiles to produce the corresponding products. Among them, palladium-catalyzed cyclization of propargylic esters with bis-nucleophiles is one of the useful methodologies for the construction of functionalized cyclic molecules in one step. Since the pioneering work reported by Tsuji in 1985, a considerable number of reactions have been reported by the use of various bis-nucleophiles. In this review, a comprehensive overview of the studies on palladium-catalyzed reactions of propargylic esters with bis-nucleophiles is described, in which various functionalized cyclic molecules can be synthesized in a regio- and stereoselective manner.
引用
收藏
页码:1835 / 1864
页数:30
相关论文
共 50 条
  • [21] An unexpected palladium-catalyzed cyclization of bis-hydroxy allylic alcohols to dioxabicyclo[2.2.2]octanes
    Zawisza, A
    Sinou, D
    TETRAHEDRON LETTERS, 2006, 47 (19) : 3271 - 3274
  • [22] Palladium-catalyzed cyclization/carbonylation of iodoarene-tethered propargyl ethers with nitroarenes for the synthesis of acetamides-functionalized benzofurans
    Ge, Xing
    Fang, Xiuyu
    Miao, Ren-Guan
    Qi, Xinxin
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2023, 428
  • [23] Stereoselective Construction of Substituted Chromans by Palladium-Catalyzed Cyclization of Propargylic Carbonates with 2-(2-Hydroxyphenyl)acetates
    Yoshida, Masahiro
    Higuchi, Mariko
    Shishido, Kozo
    ORGANIC LETTERS, 2009, 11 (20) : 4752 - 4755
  • [24] Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters
    Zhang, Zhi
    Ji, Miao-Miao
    Wu, Xiao-Feng
    He, Yong-Yu
    Peng, Jin-Bao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12) : 9001 - 9010
  • [25] Palladium-catalyzed cascade cyclization of allenamide with 2-iodoanilines to access functionalized indoloquinolines
    Geng, Wenzhe
    Wang, Hui
    Xi, Juan
    Jiang, Ruonan
    Guo, Jintao
    Jiao, Keqiang
    Tang, Mengyao
    Liu, Qing
    Zhang, Lizhi
    Liu, Hui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (02) : 279 - 283
  • [26] Palladium-Catalyzed Cyclization Reaction of Oxime Acetates and Aryl Iodides: Syntheses of 2-Imidazolines
    Hu, Jinxing
    Li, Zefei
    Zhang, Xian
    Han, Yufei
    Liu, Yue
    Zhao, Yanfang
    Liu, Yajing
    Gong, Ping
    ORGANIC LETTERS, 2018, 20 (07) : 2116 - 2119
  • [27] Palladium-Catalyzed Allylic Alkylation Reactions of Glycolates as a Tool for the Synthesis of Functionalized -Hydroxy Esters
    Kiefer, Alexander
    Gawas, Dnyaneshwar
    Kazmaier, Uli
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (26) : 5810 - 5816
  • [28] Flexible Strategy for Syntheses of Spirooxindoles using Palladium-Catalyzed Carbosilylation and Sakurai-Type Cyclization
    Hande, Sudhir M.
    Nakajima, Motoyuki
    Kamisaki, Haruhi
    Tsukano, Chihiro
    Takemoto, Yoshiji
    ORGANIC LETTERS, 2011, 13 (07) : 1828 - 1831
  • [29] SYNTHESIS OF DIHYDROBENZO [1,4] OXAZINES BY PALLADIUM-CATALYZED CYCLIZATION OF N-SUBSTITUTED 2-AMINOPHENOLS WITH PROPARGYLIC CARBONATES
    Yoshida, Masahiro
    Mori, Shunya
    Matsumoto, Kenji
    Hirokane, Tsukasa
    HETEROCYCLES, 2020, 101 (02) : 435 - 443
  • [30] New and Efficient Synthesis of 1,3-Dienylphosphonates by Palladium-Catalyzed Substitution of Propargylic Esters to Diethyl Phosphite
    Liu, Xiao-Ning
    Guo, Wei-Lei
    Hou, Chuan-Jin
    Hu, Xiang-Ping
    SYNTHETIC COMMUNICATIONS, 2013, 43 (19) : 2622 - 2626