Gold(I)-catalyzed synthesis of dihydrobenzofurans from aryl allyl ethers

被引:56
|
作者
Reich, Nicholas W. [1 ]
Yang, Cai-Guang [1 ]
Shi, Zhangjie [1 ]
He, Chuan [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
homogeneous catalysis; gold; cyclization; alkenes; Claisen rearrangement;
D O I
10.1055/s-2006-932491
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Formation of dihydrobenzofurans from aryl allyl ethers was catalyzed by in situ generated PPh3AuOTf. This reaction appears to proceed by a Claisen rearrangement, followed by addition of the resulting phenol to the allyl group.
引用
收藏
页码:1278 / 1280
页数:3
相关论文
共 50 条
  • [21] Gold(I)-catalyzed hydroindolylation of allenyl ethers
    Kona, Chandrababu Naidu
    Shinde, Mahesh H.
    Ramana, Chepuri V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (19) : 5358 - 5362
  • [22] Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers
    Niki, Yuta
    Mitsudo, Koichi
    Sato, Eisuke
    Suga, Seiji
    ORGANIC LETTERS, 2024, 26 (51) : 11111 - 11116
  • [23] Gold(I)-catalyzed cyclizations of silyl enol ethers: Application to the synthesis of (+)-lycopladine A
    Staben, Steven T.
    Kennedy-Smith, Joshua J.
    Huang, David
    Corkey, Britton K.
    LaLonde, Rebecca L.
    Toste, F. Dean
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) : 5991 - 5994
  • [24] Gold(I)-Catalyzed Synthesis of Unsymmetrical Ethers Using Alcohols as Alkylating Reagents
    Liu, Yongxiang
    Wang, Xiaoyu
    Wang, Yanshi
    Du, Chuan
    Shi, Hui
    Jin, Shengfei
    Jiang, Chongguo
    Xiao, Jianyong
    Cheng, Maosheng
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) : 1029 - 1036
  • [25] Observations on the rearrangement of allyl aryl ethers
    Hurd, CD
    Schmerling, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 107 - 109
  • [26] CLAISEN REARRANGEMENT OF ALLYL ARYL ETHERS
    STRESINKA, J
    CHEMICKE ZVESTI, 1976, 30 (02): : 237 - 245
  • [27] REACTION OF HYDROSILANES WITH ALLYL ARYL ETHERS
    BELYAKOVA, ZV
    POMERANTSEVA, MG
    BYKOVCHENKO, VG
    CHERNYSHEV, EA
    ZHURNAL OBSHCHEI KHIMII, 1976, 46 (05): : 1034 - 1040
  • [28] ASYMMETRIC DIHYDROXYLATION OF ARYL ALLYL ETHERS
    WANG, ZM
    ZHANG, XL
    SHARPLESS, KB
    TETRAHEDRON LETTERS, 1993, 34 (14) : 2267 - 2270
  • [29] Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals
    Pati, Kamalkishore
    Gomes, Gabriel dos Passos
    Harris, Trevor
    Alabugin, Igor V.
    ORGANIC LETTERS, 2016, 18 (05) : 928 - 931
  • [30] Synthesis of Allyl Ethers from Allyl Chloride with Alcohols Catalyzed by Copper-Zirconium Oxide Supported PdO
    Yuan Enxian
    Sang Ruishi
    Jian Panming
    ChinaPetroleumProcessing&PetrochemicalTechnology, 2021, 23 (04) : 65 - 74