Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones

被引:17
|
作者
Shintani, Ryo [1 ]
Tsuji, Takaoki [1 ]
Park, Soyoung [1 ]
Hayashi, Tamio [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
关键词
ALLYLATION; ALKYLATION; INDOLES; INTERMEDIATE; CYCLIZATION; GENERATION; REAGENTS; ALCOHOLS; ACETATES; KETONES;
D O I
10.1039/b924416f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed intramolecular decarboxylative cyclization of alpha-aryl-gamma-methylidene-delta-valerolactones, followed by olefin isomerization, has been developed to give fused polycyclic aromatic compounds under mild conditions. The process described here can be regarded as a formal decarboxylative allylic arylation without using a pre-formed organometallic nucleophile. The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease.
引用
收藏
页码:1697 / 1699
页数:3
相关论文
共 50 条
  • [31] Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Dihydroquinolinones
    Trost, Barry M.
    Nagaraju, Anugula
    Wang, Feijun
    Zuo, Zhijun
    Xu, Jiayi
    Hull, Kami L.
    ORGANIC LETTERS, 2019, 21 (06) : 1784 - 1788
  • [32] Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones
    Craig, Robert A., II
    Loskot, Steven A.
    Mohr, Justin T.
    Behenna, Douglas C.
    Harned, Andrew M.
    Stoltz, Brian M.
    ORGANIC LETTERS, 2015, 17 (21) : 5160 - 5163
  • [33] Palladium-Catalyzed Decarboxylative Coupling of Allylic Alkynoates with Arynes
    Pi, Shao-Feng
    Tang, Bo-Xiao
    Li, Jin-Heng
    Liu, Yi-Lin
    Liang, Yun
    ORGANIC LETTERS, 2009, 11 (11) : 2309 - 2312
  • [34] Palladium-catalyzed alkoxycarbonylation of aryl- and alkenyliodonium salts
    Kang, SK
    Yamaguchi, T
    Ho, PS
    Kim, WY
    Ryu, HC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (05): : 841 - 842
  • [35] Fluoradenes via palladium-catalyzed intramolecular arylation
    Rong, Lingling
    Liu, Qiancai
    Shi, Yingbo
    Tang, Jie
    CHEMICAL COMMUNICATIONS, 2011, 47 (07) : 2155 - 2157
  • [36] Palladium-catalyzed [4+2] cycloaddition of sulfamate-derived cyclic imines with γ-methylidene-δ-valerolactones/2-methylidenetrimethylene carbonate
    Huang, Ke-Xin
    Wu, Wen-Jie
    Chen, Zhao-Yang
    Du, Jia
    Gao, Wen-Chao
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (07) : 1035 - 1044
  • [37] Asymmetric Palladium-Catalyzed Intramolecular α-Arylation of Aldehydes
    Garcia-Fortanet, Jorge
    Buchwald, Stephen L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8108 - 8111
  • [38] Palladium-Catalyzed Intramolecular Decarboxylative Coupling of Arene Carboxylic Acids/Esters with Aryl Bromides
    Shen, Zengming
    Ni, Zhenjie
    Mo, Song
    Wang, Jing
    Zhu, Yamin
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4859 - 4865
  • [39] Palladium-catalyzed α-arylation of aldehydes with aryl bromides
    Terao, Y
    Fukuoka, Y
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON LETTERS, 2002, 43 (01) : 101 - 104
  • [40] Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones
    Cao, Xiangxiang
    Bai, Yang
    Xie, Yanjun
    Deng, Guo-Jun
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 383 : 94 - 100