Catalyst-free arylation of sulfonamides via visible light-mediated deamination

被引：21
|
作者：
Luo, Yong [1 ]
Ding, Hao [2 ]
Zhen, Jing-Song [1 ]
Du, Xian [1 ]
Xu, Xiao-Hong [1 ]
Yuan, Han [1 ]
Li, Yi-Hui [1 ]
Qi, Wan-Ying [1 ]
Liu, Bing-Zhe [1 ]
Lu, Shi-Man [1 ]
Xue, Can [3 ]
Ding, Qiuping [2 ]
机构：
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci Shenzhen, Guangzhou 510275, Peoples R China
[2] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China
[3] Sun Yat Sen Univ, Sch Chem Engn & Technol, Zhuhai 519082, Peoples R China
来源：
CHEMICAL SCIENCE | 2021年 / 12卷 / 27期
基金：
中国国家自然科学基金;
关键词：
SULFUR-DIOXIDE SURROGATE; DIARYL SULFONES; BORONIC ACIDS; SULFONYLATION; ACTIVATION; NITROGEN; CLEAVAGE; AMIDES;
D O I：
10.1039/d1sc02266k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel arylation of sulfonamides with boronic acids to afford numerous diaryl sulfones via a visible light-mediated N-S bond cleavage other than the typical transition-metal-catalyzed C(O)-N bond activation is described. This methodology, which represents the first catalyst-free protocol for the sulfonylation of boronic acids, is characterized by its simple reaction conditions, good functional group tolerance and high efficiency. Several successful examples for the late-stage functionalization of diverse sulfonamides indicate the high potential utility of this method in pharmaceutical science and organic synthesis.
引用
收藏
页码：9556 / 9560
页数：5
相关论文
共 50 条
  • [21] Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines
    Huang, Yang
    Lei, Yun-Yun
    Zhao, Liang
    Gu, Jiwei
    Yao, Qiuli
    Wang, Ze
    Li, Xiao-Fei
    Zhang, Xingang
    He, Chun-Yang
    CHEMICAL COMMUNICATIONS, 2018, 54 (97) : 13662 - 13665
  • [22] Visible-Light Promoted Catalyst-Free Imidation of Arenes and Heteroarenes
    Song, Lu
    Zhang, Long
    Luo, Sanzhong
    Cheng, Jin-Pei
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) : 14231 - 14234
  • [23] Thiochromane Formation via Visible-Light-Mediated Intramolecular ?-C(sp3)-H Bond Arylation of Sulfonamides
    Liu, Shuai
    Kumar, Nivesh
    Robert, Frederic
    Landais, Yannick
    ORGANIC LETTERS, 2023, 25 (17) : 3072 - 3077
  • [24] Visible-light mediated, catalyst-free synthesis of 3-indolyl-3-hydroxy oxindoles in water
    Tavakolian, Mina
    Hosseini-Sarvari, Mona
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2020, 18
  • [25] Visible-light-mediated catalyst-free synthesis of trifluoromethyl(spiro)-epoxides bearing contiguous quaternary centers
    Lin, Jingchuan
    Zhang, Yu
    Wang, Jinxin
    Han, Xinyu
    Zhu, Shenglan
    Li, Tong
    Zhu, Yanping
    Zhang, Wei-Dong
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (11) : 3080 - 3088
  • [26] Visible Light-mediated Direct Arylation of Arenes and Heteroarenes Using Diaryliodonium Salts in the Presence and Absence of a Photocatalyst
    Tobisu, Mamoru
    Furukawa, Takayuki
    Chatani, Naoto
    CHEMISTRY LETTERS, 2013, 42 (10) : 1203 - 1205
  • [27] Development of Transiently Strainable Benzocycloheptenes for Catalyst-Free, Visible-Light-Mediated [3+2]-Cycloadditions
    Kharbanda, Shivangi
    Alkhamayseh, Osaid
    Eastham, Georgia
    Weaver, Jimmie D.
    BIOCONJUGATE CHEMISTRY, 2025, 36 (02) : 302 - 308
  • [28] Visible Light-Mediated Cyclopropanation: Recent Progress
    Chen, Ze-Le
    Xie, Yang
    Xuan, Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (44)
  • [29] Visible Light-Mediated Construction of Sulfonated Dibenzazepines
    Qu, Chuan-Hua
    Song, Gui-Ting
    Ou, Jian-Hua
    Tang, Dian-Yong
    Xu, Zhi-Gang
    Chen, Zhong-Zhu
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (08) : 2220 - 2226
  • [30] Visible Light-Mediated Coupling of α-Bromochalcones with Alkenes
    Paria, Suva
    Kais, Viktor
    Reiser, Oliver
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2853 - 2858
12345