Photocatalytic Aerobic Oxysulfonylation of Alkynes to Access β-Keto Sulfones Catalyzed by OVs-N-Nb2O5

被引:11
作者
Song, Tao [1 ]
Zhang, Yinpan [1 ]
Wang, Chun [2 ]
Li, Yafei [2 ]
Yang, Yong [1 ]
机构
[1] Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, CAS Key Lab Biobased Mat, Shandong Energy Inst,Qingdao New Energy Shandong, Qingdao 266101, Shandong, Peoples R China
[2] Nanjing Normal Univ, Sch Chem & Mat Sci, Nanjing 210023, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Oxygen vacancies; Semiconducts; Photocatalysis; Oxysulfonylation of alkynes; beta-Keto sulfones; SULFINIC ACIDS; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; EFFICIENT; ALKENES; OXIDATION; DIFUNCTIONALIZATION; DIOXYGEN; SULFONYLATION; INHIBITORS;
D O I
10.1002/cjoc.202200410
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a novel heterogeneous photocatalyst for radical-mediated oxidative oxysulfonylation of alkynes to beta-keto sulfones under environmentally benign conditions. The oxygen vacancy-rich semiconductor Nb2O5 (labeled as OVs-N-Nb2O5) could efficiently catalyze a wide range of alkynes, especially for those bearing electron-deficient substituents or internal alkynes, to their corresponding beta-keto sulfones in good to high yields with good tolerance of diverse functional groups under visible-light illumination. The late-stage modification of steroidal compounds and synthesis of bioactive molecules were also achieved via this procedure, highlighting its potential for practical applications. Meanwhile, the photocatalyst OVs-N-Nb2O5 showed outstanding catalytic stability for successive recycles without appreciable loss in activity and selectivity. The critical role of oxygen vacancies on improving reaction activity and selectivity was clearly disclosed via control experiments and theoretical calculation.
引用
收藏
页码:2618 / 2624
页数:7
相关论文
共 49 条
  • [11] Novel and Efficient Chromium(II)-Mediated Desulfonylation of α-Sulfonyl Ketone
    Inanaga, Kazato
    Fukuyama, Takashi
    Kubota, Manabu
    Komatsu, Yuki
    Chiba, Hiroyuki
    Kayano, Akio
    Tagami, Katsuya
    [J]. ORGANIC LETTERS, 2015, 17 (12) : 3158 - 3161
  • [12] Heterojunction semiconductors: A strategy to develop efficient photocatalytic materials for visible light water splitting
    Jang, Jum Suk
    Kim, Hyun Gyu
    Lee, Jae Sung
    [J]. CATALYSIS TODAY, 2012, 185 (01) : 270 - 277
  • [13] Building a Pyrazole-Benzothiadiazole-Pyrazole Photosensitizer into Metal-Organic Frameworks for Photocatalytic Aerobic Oxidation
    Jin, Ji-Kang
    Wu, Kun
    Liu, Xin-Yi
    Huang, Guo-Quan
    Huang, Yong-Liang
    Luo, Dong
    Xie, Mo
    Zhao, Yifang
    Lu, Weigang
    Zhou, Xiao-Ping
    He, Jian
    Li, Dan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (50) : 21340 - 21349
  • [14] Application of Fundamental Organometallic Chemistry to the Development of a Gold-Catalyzed Synthesis of Sulfinate Derivatives**
    Johnson, Miles W.
    Bagley, Scott W.
    Mankad, Neal P.
    Bergman, Robert G.
    Mascitti, Vincent
    Toste, F. Dean
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (17) : 4404 - 4407
  • [15] Oxidation of sulfides to sulfoxides. Part 2: Oxidation by hydrogen peroxide
    Kaczorowska, K
    Kolarska, Z
    Mitka, K
    Kowalski, P
    [J]. TETRAHEDRON, 2005, 61 (35) : 8315 - 8327
  • [16] Kalir A., 1993, SULPHUR CONTAINING F, P957, DOI [10.1002/9780470034408.ch16, DOI 10.1002/9780470034408.CH16]
  • [17] Efficient conversion of sulfones into β-keto sulfones by N-acylbenzotriazoles
    Katritzky, AR
    Abdel-Fattah, AAA
    Wang, MY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) : 1443 - 1446
  • [18] Amino Acid-Catalyzed Direct Synthesis of β-Keto Sulfones via Aerobic Difunctionalization of Terminal Alkynes in an Aqueous Medium
    Kumar, Navaneet
    Kumar, Atul
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (10) : 9182 - 9188
  • [19] Selective Organic Transformations over Cadmium Sulfide-Based Photocatalysts
    Li, Jing-Yu
    Li, Yue-Hua
    Qi, Ming-Yu
    Lin, Qiong
    Tang, Zi-Rong
    Xu, Yi-Jun
    [J]. ACS CATALYSIS, 2020, 10 (11) : 6262 - 6280
  • [20] Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward β-Keto Sulfones
    Lu, Qingquan
    Zhang, Jian
    Zhao, Ganglu
    Qi, Yue
    Wang, Huamin
    Lei, Aiwen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (31) : 11481 - 11484