Visible-Light-Induced and Iodoform-Promoted Functionalization of Ether with Secondary Sulfonyl Amides

被引:2
|
作者
Zhang, Fengrong [1 ]
Liu, Lanqin [1 ]
Chen, Xiaoyun [2 ]
Hou, Hong [1 ]
Han, Ying [1 ]
Yan, Chaoguo [1 ]
Shi, Yaocheng [1 ]
Zhu, Shaoqun [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225009, Peoples R China
[2] Jiangsu Univ Sci & Technol, Sch Environm & Chem Engn, Zhenjiang 212005, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 01期
基金
中国国家自然科学基金;
关键词
C-H AMINATION; N BOND-FORMATION; HEMIAMINAL ETHERS; ALKYL ETHERS; AZOLES; CYCLIZATION; TETRAZOLES; ADJACENT; STRATEGY;
D O I
10.1021/acs.joc.3c01545
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An iodoform-promoted functionalization of ether with secondary sulfonyl amides under visible-light irradiation was developed toward synthesis of hemiaminal skeleton with good to excellent isolated yields. The characterization of the isolated ether and iodoform complex revealed regioselective hydrogen atom transfer to initiate carbon radical formation and enabled the amination reaction with the sulfonamide.
引用
收藏
页码:687 / 691
页数:5
相关论文
共 50 条
  • [31] Introducing N-Sulfinylamines into Visible-Light-Induced Carbene Chemistry for the Synthesis of Diverse Amides and α-Iminoesters
    Roy, Sourav
    Biswas, Apurba
    Paul, Hrishikesh
    Ariyan, S. k
    Chatterjee, Indranil
    ORGANIC LETTERS, 2023, 25 (47) : 8511 - 8515
  • [32] Visible-Light-Induced Iminothiolation of Unactivated Alkenes
    Wang, Ding-Xing
    Cai, Sai-Hu
    Liu, Haidong
    Ye, Lu
    Zhu, Chuan
    Feng, Chao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1386 - 1389
  • [33] Visible-Light-Induced Acetalization of Aldehydes with Alcohols
    Yi, Hong
    Niu, Linbin
    Wang, Shengchun
    Liu, Tianyi
    Singh, Atul K.
    Lei, Aiwen
    ORGANIC LETTERS, 2017, 19 (01) : 122 - 125
  • [34] Visible-light-induced installation of oxyfluoroalkyl groups
    Park, Gwi-Rim
    Moon, Jisu
    Cho, Eun Jin
    CHEMICAL COMMUNICATIONS, 2017, 53 (95) : 12786 - 12789
  • [35] Visible-light-induced reactions of methylenecyclopropanes (MCPs)
    Wei, Hao-Zhao
    Shi, Min
    Wei, Yin
    CHEMICAL COMMUNICATIONS, 2023, 59 (19) : 2726 - 2738
  • [36] Visible-Light-Induced Passerini Multicomponent Polymerization
    Tuten, Bryan T.
    De Keer, Lies
    Wiedbrauk, Sandra
    Van Steenberge, Paul H. M.
    D'hooge, Dagmar R.
    Barner-Kowollik, Christopher
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (17) : 5672 - 5676
  • [37] Visible-Light-Induced Intermolecular Oxyimination of Alkenes
    Li, Jun
    Yuan, Yong
    Bao, Xiazhen
    Sang, Tongzhi
    Yang, Jie
    Huo, Congde
    ORGANIC LETTERS, 2021, 23 (09) : 3712 - 3717
  • [38] Visible-Light-Induced Trifluoromethylation of Allylic Alcohols
    Li, Bowen
    Zeng, Wubing
    Wang, Lin
    Geng, Zhishuai
    Loh, Teck-Peng
    Xie, Peizhong
    ORGANIC LETTERS, 2021, 23 (13) : 5235 - 5240
  • [39] Visible-light-induced oxytrifluoromethylthiolation of α-diazo esters
    Tan, Fei
    Yang, Jian
    Song, Tao
    Hou, Zhangqun
    Huang, Xiao
    Wang, Jian
    Mei, Ling
    Dong, Hongbo
    GREEN CHEMISTRY, 2025, 27 (11) : 2989 - 2994
  • [40] Visible-Light-Induced Meerwein Fluoroarylation of Styrenes
    Tang, Hai-Jun
    Zhang, Bin
    Xue, Fei
    Feng, Chao
    ORGANIC LETTERS, 2021, 23 (10) : 4040 - 4044