Ru(II)-Catalyzed Synthesis of Substituted Furans and Their Conversion to Butenolides

被引:12
|
作者
El Arba, Marie [1 ]
Dibrell, Sara E. [1 ]
Meece, Frederick [1 ]
Frantz, Doug E. [1 ]
机构
[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA
基金
美国国家科学基金会;
关键词
POLYSUBSTITUTED FURANS; MULTISUBSTITUTED FURANS; REGIOSELECTIVE SYNTHESIS; DIAZOCARBONYL COMPOUNDS; CATALYTIC CONVERSION; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; ALKYNES; CYCLIZATION; PYRROLES;
D O I
10.1021/acs.orglett.8b02554
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of densely functionalized trisubstituted and tetrasubstituted furans via a novel Ru(II)-catalyzed intramolecular cyclization of vinyl diazoesters is reported. The synthetic utility of these furans is further demonstrated through a simple acid-mediated reaction to access highly substituted Delta alpha,beta-butenolides.
引用
收藏
页码:5886 / 5888
页数:3
相关论文
共 50 条
  • [31] 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
  • [32] An efficient synthesis of 2,5-diimino-furans via Pd-catalyzed cyclization of bromoacrylamides and isocyanides
    Jiang, Huanfeng
    Yin, Meizhou
    Li, Yibiao
    Liu, Bifu
    Zhao, Jinwu
    Wu, Wanqing
    CHEMICAL COMMUNICATIONS, 2014, 50 (16) : 2037 - 2039
  • [33] Calcium-Catalyzed Synthesis of Fused Furo[2,3-b]furans and Substituted Furans from 2-Oxo Aldehydes and Cyclic Enols
    Yaragorla, Srinivasarao
    Ithu, Sanyasi Rao
    Arun, Doma
    Srivardhan, Valmuri
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24) : 16817 - 16828
  • [34] Gold-Catalyzed Cycloisomerization of (2-Alkynyl-1-cycloalkenyl)methanols to Highly Substituted Furans
    Oh, Chang Ho
    Yi, Hyun Jik
    Lee, Kyu Hwan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (03): : 683 - 688
  • [35] A Highly Efficient Synthesis of 2,5-Disubstituted Furans from Enyne Acetates Catalyzed by Lewis Acid and Palladium
    Chen, Zhang-Wang
    Luo, Miao-Ting
    Wen, Yue-Lu
    Ye, Min
    Zhou, Zhong-Gao
    Liu, Liang-Xian
    SYNLETT, 2014, 25 (16) : 2341 - 2344
  • [36] Synthesis of Furans via Rhodium(III)-Catalyzed Cyclization of Acrylic Acids with α-Diazocarbonyl Compounds
    Hong, Chao
    Yu, Shuling
    Liu, Zhanxiang
    Xu, Zijing
    Zhang, Yuhong
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18) : 11979 - 11988
  • [37] Synthesis of Polysubstituted Furans from α-Substituted 2-Enals
    Fedoseeva, V. G.
    Verochkina, E. A.
    Larina, L. I.
    Vchislo, N. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (11) : 2157 - 2161
  • [38] Ru(ii)-Catalyzed cascade decarbonylative annulation and dehydrogenative alkenylation reactions: synthesis of phthalides†
    Baruah, Swagata
    Sultana, Sabera
    Bhorali, Pratiksha
    Saikia, Pallabi
    Gogoi, Sanjib
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (13) : 2997 - 3003
  • [39] Gold-Catalyzed Regioselective Synthesis of 2- and 3-Alkynyl Furans
    Li, Yifan
    Brand, Jonathan P.
    Waser, Jerome
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (26) : 6743 - 6747
  • [40] Ru-catalyzed synthesis of substituted phthalides through C-H bond activation and functionalization
    Kianmehr, Ebrahim
    Fardpour, Maryam
    Darvish, Ali
    Kharat, Ali Nemati
    Ng, Seik Weng
    TETRAHEDRON LETTERS, 2019, 60 (10) : 699 - 702