Iodotriphenylphosphonium iodide mediated deprotection of aryl alkyl ethers under metal-free and neutral conditions

被引:0
|
作者
Zhang, Minxiang [1 ]
Xie, Hongyan [1 ]
Yan, Zhaohua [1 ]
Fang, Xueyu [1 ]
Fang, Yongsong [2 ]
机构
[1] Nanchang Univ, Coll Chem & Chem Engn, Nanchang 330031, Jiangxi, Peoples R China
[2] Zhejiang Charioteer Pharmaceut Co Ltd, Xianju 317321, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
Iodotriphenylphosphonium iodide; Aryl alkyl ethers; Deprotection; Metal -free conditions; Phenols; VERSATILE REAGENTS; SYNTHETIC METHODS; BOND-CLEAVAGE; BENZYL ETHERS; IONIC LIQUID; TRIPHENYLPHOSPHINE; EPOXIDES; ALLYL; DEALKYLATION; DEOXYGENATION;
D O I
10.1016/j.tetlet.2023.154460
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient method for the deprotection of aryl alkyl ethers under metal-free and neutral condi-tions was developed by iodotriphenylphosphonium iodide [Ph3P+I]I- formed in situ through the reaction of equimolar PPh3 and I2. A variety of aryl alkyl ethers including aryl methyl/allyl/benzyl/ethyl/n-propyl/ i-propyl/n-butyl ethers can all be highly efficiently deprotected to release the corresponding phenols in good to excellent yields.(c) 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [31] Electrochemical Synthesis of Aryl Sulfonates from Sodium Sulfinates and Phenols under Metal-Free Conditions
    Fu Zhengjiang
    Yang Zhenjiang
    Sun Li
    Yin Jian
    Yi Xuezheng
    Cai Hu
    Lei Aiwen
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (02) : 600 - 606
  • [32] Synthesis of Aryl Sulfides by Metal-Free Arylation of Thiols with Diaryliodonium Salts under Basic Conditions
    Sarkar, Sudeep
    Wojciechowska, Natalia
    Rajkiewicz, Adam A.
    Kalek, Marcin
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (02)
  • [33] Stereoselective metal-free catalytic synthesis of chiral trifluoromethyl aryl and alkyl amines
    Genoni, Andrea
    Benaglia, Maurizio
    Massolo, Elisabetta
    Rossi, Sergio
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (75) : 8365 - 8367
  • [34] Photo-Induced Carbonylation of Aryl Bromides for the Synthesis of Aryl Esters and Amides Under Transition Metal-Free Conditions
    Zheng, Yan
    Teng, Bing-Hong
    Zhang, Youcan
    Wu, Xiao-Feng
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (21)
  • [35] Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions
    Zhao, Guangkuan
    Yuan, Ling-Zhi
    Alami, Mouad
    Provot, Olivier
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2522 - 2536
  • [36] Recyclable Hypervalent-lodine-Mediated Dehydrogenative Cyclopropanation under Metal-Free Conditions
    Duan, Ya-Nan
    Zhang, Zhao
    Zhang, Chi
    [J]. ORGANIC LETTERS, 2016, 18 (23) : 6176 - 6179
  • [37] Selectfluor-mediated synthesis of isoindoline fused with triazoles under metal-free conditions
    Zhang, Hong-Ping
    Wang, Xia
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2015, (03) : 187 - 189
  • [38] Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions
    Song, Yang
    Zhang, Hao
    Guo, Jiabao
    Shao, Yifei
    Ding, Yuzhou
    Zhu, Li
    Yao, Xiaoquan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5914 - 5921
  • [39] Hypervalent iodine mediated oxidative radical amination of heteroarenes under metal-free conditions
    Zhao, Feng
    Sun, Ting
    Sun, Hefeng
    Xi, Gaolei
    Sun, Kai
    [J]. TETRAHEDRON LETTERS, 2017, 58 (32) : 3132 - 3135
  • [40] An Approach to Quinoline-Fused Imidazopyridines via CDC of Ethers with Imidazopyridines under Metal-Free Conditions
    Lian, Guifang
    Li, Jingyu
    Liu, Ping
    Sun, Peipei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24): : 16346 - 16354