Metal-Free Synthesis of Methylene-Bridged Bisamide via Selectfluor-Mediated Oxidative Methylenation

被引：16
|
作者：
Yan, Min [1 ]
Zhou, Dongheng [1 ,2 ]
Gao, Yejun [1 ]
Ma, Yongmin [1 ]
机构：
[1] Zhejiang Chinese Med Univ, Sch Pharmaceut Sci, Hangzhou 310053, Zhejiang, Peoples R China
[2] Zhejiang Univ, Dept Biochem & Mol Biol, Hangzhou 310058, Zhejiang, Peoples R China
来源：
CHEMISTRYSELECT | 2018年 / 3卷 / 46期
关键词：
Amides; DMSO; methylenebisamides; methylenation; Selectfluor; C-N CLEAVAGE; BIS-1,3-DICARBONYL COMPOUNDS; GOLD; DMSO; DISCOVERY; ACCESS; AMINES; BONDS;
D O I：
10.1002/slct.201802450
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A direct methylenation of amides to afford methylene-bridged bisamides mediated by Selectfluor in the presence of dimethyl sulfoxide (DMSO) was achieved. DMSO plays a dual role in this reaction, as both solvent and a methylene source. The developed protocol avoids the use of transition metal catalysts and the reaction is efficient, operationally convenient and tolerable in air and water.
引用
收藏
页码：13006 / 13009
页数：4
相关论文
共 50 条
  • [31] Metal-free synthesis of carboxamides via the Lossen rearrangement
    Li, Chong
    Liu, Yi-Fei
    Yang, Wei
    Zhao, Lian-Jie
    Song, Lin-Yuan
    Deng, Yu-Shuang
    Mou, Ke-Yu
    Wang, Jing-Wen
    Cao, Sheng
    Li, Feng
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (05): : 1550 - 1555
  • [32] One-pot synthesis of heteroaromatic acetals via selectfluor-mediated tandem reaction of methyl quinoline-2-carboxylate and methanol
    Wang, Wengui
    Chen, Zhenqiang
    Zhang, Yingying
    Zeng, Wei
    Wang, Shoufeng
    TETRAHEDRON, 2022, 105
  • [33] Synthesis of β-keto-sulfones via metal-free TBAI/TBHP mediated oxidative cross-coupling of vinyl acetates with sulfonylhydrazides
    Tang, Yucai
    Fan, Yuanyuan
    Gao, Hongjie
    Li, Xiaoqing
    Xu, Xiangsheng
    TETRAHEDRON LETTERS, 2015, 56 (41) : 5616 - 5618
  • [34] Visible light-mediated syntheses of unsymmetrical methylene-bridged bis-heterocycles via an alkoxy radical relay reaction
    Yuan, Ting-Ting
    Chen, Jing
    Pham, Le Nhan
    Paul, Sayan
    White, Lorenzo V.
    Li, Jialong
    Lan, Ping
    Coote, Michelle L.
    Banwell, Martin G.
    He, Yu-Tao
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (18) : 4649 - 4657
  • [35] Hypervalent Iodine-mediated/Catalyzed Oxidative Cycloisomerization/Annulation of Alkynes for Metal-free Synthesis of Oxazoles
    Saito, Akio
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (18) : 2048 - 2069
  • [36] Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
    Smyrnov, Vladyslav
    Muriel, Bastian
    Waser, Jerome
    ORGANIC LETTERS, 2021, 23 (14) : 5435 - 5439
  • [37] Selectfluor-Promoted Sequential Reactions via Allene Intermediates: Metal-Free Construction of Fused Polycyclic Skeletons
    Liu, Le
    Wang, Jianbo
    Zhou, Hongwei
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4749 - 4753
  • [38] Synthesis, characterization and electrochemistry of succinyloxyl-bridged metal-free and transition metal porphyrin dimers
    Cheng, Xiuli
    Li, Ying
    Shi, Yuhua
    Shi, Tongshun
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2006, 36 (09) : 673 - 679
  • [39] Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
    Parumala, Santosh Kumar Reddy
    Peddinti, Rama Krishna
    TETRAHEDRON LETTERS, 2016, 57 (11) : 1232 - 1235
  • [40] Metal-Free Synthesis of 2-Aminobenzothiazoles via Aerobic Oxidative Cyclization/Dehydrogenation of Cyclohexanones and Thioureas
    Zhao, Jinwu
    Huang, Huawen
    Wu, Wanqing
    Chen, Huoji
    Jiang, Huanfeng
    ORGANIC LETTERS, 2013, 15 (11) : 2604 - 2607
12345