Iron-Catalyzed Oxyphosphorylation of Styrenes to Access β-Ketophosphonates and α, β-Unsaturated Ketones

被引:3
|
作者
Zhao, Yukun [1 ]
Xu, Jingwen [1 ]
Chen, Hongbing [1 ]
Xia, Yi [1 ]
Hu, Lin [1 ,2 ]
机构
[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Key Lab Chem Genom, Shenzhen 518055, Guangdong, Peoples R China
关键词
Iron; Aerobic oxidation; beta-Ketophosphonates; alpha; beta-Unsaturated carbonyl compounds; AEROBIC OXYPHOSPHORYLATION; CARBONYL-COMPOUNDS; PHOSPHONATES; ACIDS; ALKYNES;
D O I
10.1002/adsc.202300733
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The first iron-catalyzed oxophosphorylation of styrene derivatives with dialkyl H-phosphonates under open air conditions is developed, which generates a range of previously underexplored asubstituted beta-ketophosphonates in 55 similar to 70% yields. Furthermore, a convenient one-pot procedure by direct conversion of styrenes to alpha, beta-unsaturated ketones is also developed based on the new catalytic reactions, thus offering a protocol to access two classes of valuable products from simple starting materials.
引用
收藏
页码:3290 / 3294
页数:5
相关论文
共 50 条
  • [31] Iron-Catalyzed Oxidative α-Amination of Ketones with Primary and Secondary Sulfonamides
    Song, Fubin
    Park, So Hyun
    Wu, Christine
    Strom, Alexandra E.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3353 - 3358
  • [32] Iron-Catalyzed Mizoroki-Heck Cross-Coupling Reaction with Styrenes
    Loska, Rafal
    Volla, Chandra M. Rao
    Vogel, Pierre
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) : 2859 - 2864
  • [33] Iron-Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes
    Savela, Risto
    Majewski, Marcin
    Leino, Reko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (19) : 4137 - 4147
  • [34] Access to Chiral HWE Reagents by Rhodium-Catalyzed Asymmetric Arylation of γ,δ-Unsaturated β-Ketophosphonates
    Yin, Long
    Zhang, Dewei
    Xing, Junhao
    Wang, Yuhan
    Wu, Changhui
    Lu, Tao
    Chen, Yadong
    Hayashi, Tamio
    Dou, Xiaowei
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10): : 5869 - 5875
  • [35] Iron Catalyzed Isomerization of α-Alkyl Styrenes to Access Trisubstituted Alkenes
    Xu, Songgen
    Liu, Guixia
    Huang, Zheng
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (03) : 585 - 589
  • [36] Photoredox-Catalyzed Oxydifluoroalkylation of Styrenes for Access to Difluorinated Ketones with DMSO as an Oxidant
    Li, Lixin
    Ma, Yan-Na
    Tang, Mi
    Guo, Jing
    Yang, Zhen
    Yan, Yizhe
    Ma, Xiantao
    Tang, Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3723 - 3728
  • [37] Iron-catalyzed Selective Oxidation of α,β-Unsaturated Aldehydes to α,β-Unsaturated Carboxylic Acids by Molecular Oxygen
    Tanaka, Shinji
    Kon, Yoshihiro
    Uesaka, Yumiko
    Morioka, Ryo
    Tamura, Masanori
    Sato, Kazuhiko
    CHEMISTRY LETTERS, 2016, 45 (02) : 188 - 190
  • [38] Iron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer
    Zhao, Han-Qing
    Li, Wan-Ting
    Yao, Yong
    Zhao, Yi-Lin
    Ouyang, Xuan-Hui
    ORGANIC LETTERS, 2024, 26 (47) : 10183 - 10188
  • [39] An efficient synthesis of diaryl ketones by iron-catalyzed arylation of aroyl cyanides
    Duplais, C
    Bures, F
    Sapountzis, I
    Korn, TJ
    Cahiez, G
    Knochel, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (22) : 2968 - 2970
  • [40] Blue-Light-Induced Iron-Catalyzed a-Alkylation of Ketones
    Abdallah, Marie-Samira
    Joly, Nicolas
    Gaillard, Sylvain
    Poater, Albert
    Renaud, Jean-Luc
    ORGANIC LETTERS, 2022, 24 (30) : 5584 - 5589