Protecting Group-Free Gold-Catalyzed Synthesis of 2-Acylidene-3-Oxindoles and Azaaurones via a Double Oxidation Strategy

被引:3
|
作者
Song, Xinlong [1 ]
Zhao, Ximei [1 ]
Zeng, Zhongyi [1 ]
Rominger, Frank [1 ]
Rudolph, Matthias [1 ]
Hashmi, A. Stephen K. [1 ]
机构
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
关键词
oxidative gold catalysis; N-oxides; one pot synthesis; gold carbene intermediates; alkynes; INDUSTRIAL PERSPECTIVE; COUNTER ANIONS;
D O I
10.1002/ijch.202300094
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot synthesis of 2-acylidene-3-oxindole and azaaurone derivatives starting from O-alkynylanilines and alkynes is presented. By means of oxidative gold catalysis the two starting materials are transferred to reactive intermediates that in situ form the target products. This double oxidation strategy enables a protecting group-free step-economic strategy towards these valuable substrate classes.
引用
收藏
页数:7
相关论文
共 30 条
  • [21] Gold-Catalyzed Synthesis of Bicyclo[3.2.0]heptenes via a Formal [3+2]/[2+2]-Annulation of Allylsilane with 4-Methoxybut-2-yn-1-ols
    Yang, Chun-Yao
    Wang, Chiou-Dong
    Tian, Shu-Fan
    Liu, Rai-Shung
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) : 1605 - 1609
  • [22] Synthesis of N-Acyl Pyridinium-N-Aminides and Their Conversion to 4-Aminooxazoles via a Gold-Catalyzed Formal (3+2)-Dipolar Cycloaddition
    Ball-Jones, Matthew P.
    Davies, Paul W.
    ORGANIC SYNTHESES, 2018, 95 : 112 - +
  • [23] Highly regioselective Ru(II)-catalyzed [3+2] spiroannulation of 1-aryl-2-naphthols with alkynes via a double directing group strategy
    Hao, Jiamao
    Ge, Yicong
    Yang, Liuqing
    Wang, Jing
    Luan, Xinjun
    TETRAHEDRON LETTERS, 2021, 71
  • [24] One-Step Synthesis of Methanesulfonyloxymethyl Ketones via Gold-Catalyzed Oxidation of Terminal Alkynes: A Combination of Ligand and Counter Anion Enables High Efficiency and a One-Pot Synthesis of 2,4-Disubstituted Thiazoles
    Wu, Gongde
    Zheng, Renhua
    Nelson, Jonathan
    Zhang, Liming
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) : 1229 - 1234
  • [25] Gold-catalyzed selective oxidation of 4-oxahepta-1,6-diynes to 2H-pyran-3(6H)-ones and chromen-3-(4H)-ones via β-gold vinyl cation intermediates
    Ji, Kegong
    Liu, Xiang
    Du, Bowen
    Yang, Fang
    Gao, Jinming
    CHEMICAL COMMUNICATIONS, 2015, 51 (51) : 10318 - 10321
  • [26] Pd-Catalyzed Dehydrogenative Aryl-Aryl Bond Formation via Double C(sp2)-H Bond Activation:, Efficient Synthesis of [3,4]-Fused Oxindoles
    Bunescu, Ala
    Piou, Tiffany
    Wang, Qian
    Zhu, Jieping
    ORGANIC LETTERS, 2015, 17 (02) : 334 - 337
  • [27] Gold-catalyzed intermolecular tandem cyclization/[4+3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines
    Rao, Fucai
    Cheng, Meng
    Hu, Zhiwei
    Chen, Xinyi
    Zhao, Suyang
    Chen, Zuliang
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (13): : 3685 - 3691
  • [28] Divergence in the Reactivity between Amine- and Phosphine-Catalyzed Cycloaddition Reactions of Allenoates with Enynals: One-Pot Gold-Catalyzed Synthesis of Trisubstituted Benzofurans from the [3+2] Cycloadduct via 1,2-Alkyl Migration and Dehydrogenation
    Kumari, A. Leela Siva
    Swamy, K. C. Kumara
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4084 - 4096
  • [29] Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors
    Tanaka, Tomonari
    Kikuta, Naoya
    Kimura, Yoshiharu
    Shoda, Shin-ichiro
    CHEMISTRY LETTERS, 2015, 44 (06) : 846 - 848
  • [30] Synthesis of N-H-Free 1,4-Dihydroisoquinoline-3(2H)-ones via Pd-Catalyzed C-H Olefination Using Polyfluorosulfinyl as the Auxiliary Group
    Chen, Yu-Hao
    Shao, Nan-Qi
    Li, Chen
    Wang, Dong-Hui
    ORGANIC LETTERS, 2020, 22 (15) : 5880 - 5884