Gold(I)-Catalyzed Tandem Cyclization-Selective Migration Reaction of 1,3-Dien-5-ynes: Regioselective Synthesis of Highly Substituted Benzenes

被引：45
|
作者：
Garcia-Garcia, Patricia [1 ]
Martinez, Alberto [1 ]
Sanjuan, Ana M. [1 ]
Fernandez-Rodriguez, Manuel A. [1 ]
Sanz, Roberto [1 ]
机构：
[1] Univ Burgos, Fac Ciencias, Dept Quim, Area Quim Organ, Burgos 09001, Spain
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 18期
关键词：
AROMATIC ENYNES; GOLD CATALYSIS; SKELETAL REARRANGEMENT; 1,2-INDOLE MIGRATIONS; 1,2-ALKYL MIGRATION; CYCLOISOMERIZATION; NAPHTHALENES; DERIVATIVES; EFFICIENT; 3-SILYLOXY-1,5-ENYNES;
D O I：
10.1021/ol202129n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly substituted benzene derivatives have been easily prepared in a regioselective way from readily available 1,3-hexadien-5-ynes through a gold(I)-catalyzed tandem reaction. The process involves an initial cyclization followed by a selective Wagner-Meerwein shift in which the migration preference seems to be determined by the ability to stabilize a positive charge.
引用
收藏
页码：4970 / 4973
页数：4
相关论文
共 38 条
  • [31] Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: Development of a tandem aldol condensation- dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones
    Lian, Jian-Jou
    Lin, Chung-Chang
    Chang, Hsu-Kai
    Chen, Po-Chiang
    Liu, Rai-Shung
    Journal of the American Chemical Society, 2006, 128 (30): : 9661 - 9667
  • [32] Thermal and metal-catalyzed cyclization of 1-substituted 3,5-dien-1-ynes via a [1,7]-hydrogen shift: Development of a tandem aldol condensation-dehydration and aromatization catalysis between 3-en-1-yn-5-al units and cyclic ketones
    Lian, Jian-Jou
    Lin, Chung-Chang
    Chang, Hsu-Kai
    Chen, Po-Chiang
    Liu, Rai-Shung
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) : 9661 - 9667
  • [33] Regioselective Synthesis of Functionalized Pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones via Tandem Post-Ugi Cyclization and Gold(I)- Catalyzed Annulation
    Singh, Sangh Priya
    Kumar, Asheesh
    Kant, Ruchir
    Srivastava, Ajay Kumar
    JOURNAL OF ORGANIC CHEMISTRY, 2022, : 12799 - 12815
  • [34] The copper(I)-catalyzed tandem reaction of o-alkynylphenyl isothiocyanates with isocyanides: a rapid synthesis of 5H-benzo[d] imidazo[5,1-b][1,3] thiazines
    Hao, Wenyan
    Zeng, Jiangbo
    Cai, Mingzhong
    CHEMICAL COMMUNICATIONS, 2014, 50 (79) : 11686 - 11689
  • [35] Rapid construction of complex tetracyclic frameworks via a gold(I)-catalyzed tandem 1,2-acyloxy migration/[3+2] cycloaddition/Friedel-Crafts type cyclization reaction of linear enynyl esters
    Sun, Haiyu
    Xu, Shiyan
    Xing, Zhimin
    Liu, Lin
    Feng, Shangbiao
    Fang, Bowen
    Xie, Xingang
    She, Xuegong
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2109 - 2113
  • [36] Indium(III) Chloride-Catalyzed Propargylation/Amination/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Highly Substituted Pyrroles from Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines
    Liu, Xiao-tao
    Huang, Lei
    Zheng, Fei-jian
    Zhan, Zhuang-ping
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (17) : 2778 - 2788
  • [37] Efficient synthesis of 2,3-dihydro-1H-pyrazoles via a highly selective Pd(0)-catalyzed coupling-cyclization reaction of terminal 2-substituted 2,3-allenyl hydrazines with aryl iodides
    Cheng, Xin
    Ma, Shengming
    CHEMICAL COMMUNICATIONS, 2009, (28) : 4263 - 4265
  • [38] Consecutive Gold(I)-Catalyzed Cyclization Reactions of o-(Buta-1,3-diyn-1-yl-)-Substituted N-Aryl Ureas: A One-Pot Synthesis of Pyrimido[1,6-a]indol-1(2H)-ones and Related Systems
    Sharp, Phillip P.
    Banwell, Martin G.
    Renner, Jens
    Lohmann, Klaas
    Willis, Anthony C.
    ORGANIC LETTERS, 2013, 15 (11) : 2616 - 2619
1234