Gold(I)-catalyzed intramolecular hydroarylation and the subsequent ring enlargement of methylenecyclopropanes to cyclobutenes

被引：24
|
作者：
Fang, Wei [1 ,2 ]
Tang, Xiang-Ying [3 ]
Shi, Min [1 ,2 ,3 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China
来源：
RSC ADVANCES | 2016年 / 6卷 / 46期
基金：
中国国家自然科学基金;
关键词：
ACID-MEDIATED CYCLOADDITION; OPENING REACTIONS; SUBSTITUTED METHYLENECYCLOPROPANES; CYCLOPROPYLMETHYL CATION; PYRROLIDINE SKELETONS; ACETYLENIC-COMPOUNDS; HIGHLY EFFICIENT; LEWIS; GOLD; CYCLIZATION;
D O I：
10.1039/c6ra02549h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The gold(I)-catalyzed intramolecular hydroarylation of methylenecyclopropanes containing aryl propargyl ethers proceeded smoothly to give 2H-chromene derivatives in good to excellent yields under mild conditions. Furthermore, in the presence of IPrAuSbF6, these 2H-chromene derivatives containing a methylenecyclopropane could undergo ring enlargement to give the corresponding cyclobutenes.
引用
收藏
页码：40474 / 40479
页数：6
相关论文
共 50 条
  • [21] Study of the E/Z selectivity of the gold(I) catalyzed alkyne hydroarylation
    Hahn, Christine
    Adeosun, Samuel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [22] Computational Insights into the Gold-Catalyzed Ring-Opening of Methylenecyclopropanes and Vinylcyclopropanes with Sulfonamides
    Liu, Yuan
    Feng, Sidi
    Bao, Xiaoguang
    CHEMCATCHEM, 2018, 10 (13) : 2817 - 2825
  • [23] Gold(I)-catalyzed intramolecular cyclopropanation of dienynes
    Nieto-Oberhuber, C
    López, S
    Muñoz, MP
    Jiménez-Núñez, E
    Buñuel, E
    Cárdenas, DJ
    Echavarren, AM
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (06) : 1694 - 1702
  • [24] Gold(I)-Catalyzed Intramolecular Rearrangement of Vinylidenecyclopropanes
    Shi, Min
    Wu, Lei
    Lu, Jian-Mei
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21): : 8344 - 8347
  • [25] Gold(I)-catalyzed domino ring-opening ring-closing hydroamination of methylenecyclopropanes (MCPs) with sulfonamides: Facile preparation of pyrrolidine derivatives
    Shi, Min
    Liu, Le-Ping
    Tang, Jie
    ORGANIC LETTERS, 2006, 8 (18) : 4043 - 4046
  • [26] Total Synthesis of (±)-2-Debromohymenin via Gold-Catalyzed Intramolecular Alkyne Hydroarylation
    Singh, Ravi P.
    Bhandari, Manojkumar R.
    Torres, Fatima M.
    Doundoulakis, Thomas
    Gout, Delphine
    Lovely, Carl J.
    ORGANIC LETTERS, 2020, 22 (09) : 3412 - 3417
  • [27] Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies
    Jean, Mickael
    van de Weghe, Pierre
    TETRAHEDRON LETTERS, 2011, 52 (27) : 3509 - 3513
  • [28] Gold-catalyzed ring enlargement and cycloisomerization of alkynylamide tethered alkylidenecyclopropanes
    Zhang, Jia-hao
    Wei, Yin
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2980 - 2985
  • [29] Rh(I)-catalyzed enantioselective intramolecular hydroarylation of unactivated ketones with aryl pinacolboronic esters
    Gallego, Gary M.
    Sarpong, Richmond
    CHEMICAL SCIENCE, 2012, 3 (04) : 1338 - 1342
  • [30] Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations
    Tarselli, Michael A.
    Liu, Ann
    Gagne, Michel R.
    TETRAHEDRON, 2009, 65 (09) : 1785 - 1789
12345