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
  • [1] Enantioselective Synthesis of Highly Substituted Furans by a Copper(II)-Catalyzed Cycloisomerization-Indole Addition Reaction
    Rauniyar, Vivek
    Wang, Z. Jane
    Burks, Heather E.
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) : 8486 - 8489
  • [2] Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins
    Shi, Yili
    Roth, Katrina E.
    Ramgren, Stephen D.
    Blum, Suzanne A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) : 18022 - +
  • [3] Base-catalyzed bis-sulfenylation of γ-substituted butenolides for the synthesis of α,α-bisthiofunctionalized butenolide derivatives
    Zhao, Jian-Qiang
    Luo, Shu-Wen
    Zhang, Xiao-Mei
    Xu, Xiao-Ying
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    TETRAHEDRON, 2017, 73 (36) : 5444 - 5450
  • [4] Ru(ii)-catalyzed synthesis of poly-substituted furans via intermolecular oxidative annulation reaction of ethyl 3-oxo-3-phenylpropanoates with aryl alkynes/heteroaryl alkynes
    Chourasiya, Mohit
    Kumar, Amrendra
    Vikram, Vikrant Nawal
    Tadigoppula, Narender
    CHEMICAL COMMUNICATIONS, 2023, 59 (63) : 9650 - 9653
  • [5] Indium trichloride catalyzed efficient one-pot synthesis of highly substituted furans
    Dey, Sumit
    Nandi, Debkumar
    Pradhan, Prasun K.
    Giri, Venkatachalam Sesha
    Jaisankar, Parasuraman
    TETRAHEDRON LETTERS, 2007, 48 (14) : 2573 - 2575
  • [6] Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
    Pace, Domenic P.
    Robidas, Raphael
    Tran, Uyen P. N.
    Legault, Claude Y.
    Thanh Vinh Nguyen
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (12) : 8154 - 8171
  • [7] Cobalt(II)-Catalyzed Electrophilic Alkynylation of 1,3-Dicarbonyl Compounds To Form Polysubstituted Furans via π-π Activation
    Roslan, Irwan Iskandar
    Sun, Jiulong
    Chuah, Gaik-Khuan
    Jaenicke, Stephan
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (04) : 719 - 726
  • [8] Sequential Synthesis of Furans from Alkynes: Successive Ruthenium(II)- and Copper(II)-Catalyzed Processes
    Zhang, Min
    Jiang, Huan-Feng
    Neumann, Helfried
    Beller, Matthias
    Dixneuf, Pierre H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (09) : 1681 - 1684
  • [9] Modular synthesis of tetra-substituted furans from alkynes, Weinreb amides, and aldehydes
    Silwal, Sajan
    Rahaim, Ronald J.
    TETRAHEDRON LETTERS, 2015, 56 (42) : 5738 - 5742
  • [10] Efficient Synthesis of Arylated Furans by a Sequential Rh-Catalyzed Arylation and Cycloisomerization of Cyclopropenes
    Wang, Xiaoming
    Lerchen, Andreas
    Daniliuc, Constantin G.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (06) : 1712 - 1716