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
来源：
SYNLETT | 2006年 / 08期
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
  • [1] Gold-catalyzed rearrangement of substituted allyl aryl ethers
    Vyvyan, James R.
    Dimmitt, Heidi E.
    Griffith, Jennifer K.
    Steffens, Laura D.
    Swanson, Rebecca A.
    TETRAHEDRON LETTERS, 2010, 51 (50) : 6666 - 6669
  • [2] Mo(CO)(6) catalyzed one-pot conversion of allyl aryl ethers to dihydrobenzofurans
    Bernard, AM
    Cocco, MT
    Onnis, V
    Piras, PP
    SYNTHESIS-STUTTGART, 1997, (01): : 41 - &
  • [3] Gold(I) Catalyzed Dearomative Claisen Rearrangement of Allyl, Allenyl Methyl, and Propargyl Aryl Ethers
    Peruzzi, Michael T.
    Lee, Stephen J.
    Gagne, Michel R.
    ORGANIC LETTERS, 2017, 19 (22) : 6256 - 6259
  • [4] Iridium(III)-catalyzed tandem Claisen rearrangement-intramolecular hydroaryloxylation of aryl allyl ethers to form dihydrobenzofurans
    Grant, VH
    Liu, B
    TETRAHEDRON LETTERS, 2005, 46 (08) : 1237 - 1239
  • [5] Copper(I)-catalyzed synthesis of ferrocenyl aryl ethers
    an der Heiden, MR
    Frey, GD
    Plenio, H
    ORGANOMETALLICS, 2004, 23 (14) : 3548 - 3551
  • [6] Palladium-catalyzed intramolecular cyclizations of aryl allyl ethers and aryl homoallyl ethers for the synthesis of benzofuran and chromene derivatives
    Youn, So Won
    Eom, Jeong Im
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3248 - U3248
  • [7] Ir(I)-Catalyzed Enantioselective Decarboxylative Allylic Etherification: A General Method for the Asymmetric Synthesis of Aryl Allyl Ethers
    Kim, Dongeun
    Reddy, Srinivasa
    Singh, Om V.
    Lee, Jae Seung
    Kong, Suk Bin
    Han, Hyunsoo
    ORGANIC LETTERS, 2013, 15 (03) : 512 - 515
  • [8] Isomerization of allyl-aryl ethers catalyzed by ruthenium complexes
    Krompiec, S
    Kuznik, N
    Bieg, T
    Adamus, B
    Majnusz, J
    Grymel, M
    POLISH JOURNAL OF CHEMISTRY, 2000, 74 (08) : 1197 - 1200
  • [9] Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
    Wang, Jingyang
    Wang, Yu
    Ding, Guangni
    Wu, Xiaoyu
    Yang, Liqun
    Fan, Sijie
    Zhang, Zhaoguo
    Xie, Xiaomin
    TETRAHEDRON LETTERS, 2021, 81
  • [10] Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers
    Istrate, Florin M.
    Gagosz, Fabien
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 878 - 885
12345