Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade

被引：84
|
作者：
Wang, Tao [1 ]
Shi, Shuai [1 ]
Rudolph, Matthias [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构：
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 10期
关键词：
alkynes; furans; gold; iodine; N-oxides; GOLD-CATALYSIS; OXIDATIVE REARRANGEMENT; ORGANOGOLD COMPOUNDS; EFFICIENT SYNTHESIS; N-HALOSUCCINIMIDES; ALKYNES; FURANS; FUNCTIONALIZATION; CYCLIZATION; CARBENOIDS;
D O I：
10.1002/adsc.201400356
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly efficient gold(I)-catalyzed cascade reaction for the synthesis of fully substituted 3-formyl-4-iodofurans has been developed. Mechanistic investigations indicate a reaction pathway that involves a direct iodination reaction of the organogold intermediate via functionalization of the Au-C(sp(2)) bond, instead of a direct iodination of the 3-formylfurans.
引用
收藏
页码：2337 / 2342
页数：6
相关论文
共 50 条
  • [21] Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols:: Highly efficient synthesis of fully substituted dihydrofurans and furans
    Liu, YH
    Song, FJ
    Song, ZQ
    Liu, MN
    Yan, B
    ORGANIC LETTERS, 2005, 7 (24) : 5409 - 5412
  • [22] Platinum(IV)-Catalyzed Regioselective Synthesis of Highly Substituted 4H-Cyclopenta[b]furans via Cascade Hetero- cyclization of 2-(1-Alkynyl)-3-aryl-2-propenals with Arylethenes
    He, Ting
    Gao, Pin
    Zhao, Shu-Chun
    Shi, You-Di
    Liu, Xue-Yuan
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 365 - 369
  • [23] Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction
    An, Juzeng
    Pedrazzani, Riccardo
    Monari, Magda
    Marin-Luna, Marta
    Silva Lopez, Carlos
    Bandini, Marco
    CHEMICAL COMMUNICATIONS, 2020, 56 (56) : 7734 - 7737
  • [24] Synthesis of Substituted 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles by Platinum-Catalyzed Cascade Cyclization/Ring Expansion of 2-Alkynyl-1-azaspiro[2.3]hexanes
    Yoshida, Masahiro
    Maeyama, Yohei
    Al-Amin, Mohammad
    Shishido, Kozo
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (14): : 5813 - 5820
  • [25] Gold(I)-Catalyzed Tandem Cyclization-Selective Migration Reaction of 1,3-Dien-5-ynes: Regioselective Synthesis of Highly Substituted Benzenes
    Garcia-Garcia, Patricia
    Martinez, Alberto
    Sanjuan, Ana M.
    Fernandez-Rodriguez, Manuel A.
    Sanz, Roberto
    ORGANIC LETTERS, 2011, 13 (18) : 4970 - 4973
  • [26] Synthesis of fused pyrrolo-heterocycles via novel gold-catalyzed cascade transformation involving 1,2-migration of silicon, tin, and germanium
    Seregin, Ilya V.
    Gevorgyan, Vladimir
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [27] Gold(III) or Gold(I)/Lewis-Acid-Catalyzed Substitution/Cyclization/1,2-Migration Reactions of Propargyl Alcohols with 3-Amino-benzo[d]isoxazoles: Synthesis of Pyrimidine Derivatives
    Wang, Ali
    Lu, Mingduo
    Xie, Xin
    Liu, Yuanhong
    ORGANIC LETTERS, 2022, 24 (15) : 2944 - 2949
  • [28] Synthesis of 1,2,5-and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization
    Kim, Jun Hee
    Lee, Sang Bin
    Lee, Won Koo
    Yoon, Doo-Ha
    Ha, Hyun-Joon
    TETRAHEDRON, 2011, 67 (19) : 3553 - 3558
  • [29] A DFT study on the mechanism of gold(III)-catalyzed synthesis of highly substituted furans via [3,3]-sigmatropic rearrangements and/or [1,2]-acyloxy migration based on propargyl ketones
    Fang, Ran
    Yang, Lizi
    Wang, Yongcheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 2760 - 2770
  • [30] Synthesis of benzyl substituted tetrahydropyridines and 1,2,3,4-tetrahydroisoquinolines via acid catalyzed cyclization of γ,δ-unsaturated N-formyl-N-styryl amines
    Meuzelaar, GJ
    Maat, L
    Sheldon, RA
    TETRAHEDRON, 1999, 55 (14) : 4481 - 4488
12345