A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

被引:12
|
作者
Wu, Ding-Chuan [1 ,2 ]
Bai, Jing-Wen [1 ,2 ]
Guo, Lei [1 ,2 ]
Hu, Guang-Qi [1 ,2 ]
Liu, Kai-Hui [1 ,2 ]
Sheng, Fei-Fei [1 ,2 ]
Zhang, Hong-Hai [1 ,2 ]
Sun, Zheng-Yi [1 ,2 ]
Shen, Kang [1 ,2 ]
Liu, Xiang [1 ,2 ]
机构
[1] Nanjing Tech Univ Nanjing Tech, Jiangsu Natl Synergist Innovat Ctr Adv Mat SICAM, Key Lab Flexible Elect KLOFE, 30 Puzhu Rd, Nanjing 211816, Peoples R China
[2] Nanjing Tech Univ Nanjing Tech, Inst Adv Mat IAM, Jiangsu Natl Synergist Innovat Ctr Adv Mat SICAM, 30 Puzhu Rd, Nanjing 211816, Peoples R China
基金
中国国家自然科学基金;
关键词
Late-stage deuteration; Terminal alkyne; Silver salt; SELECTIVE DEUTERATION; H FUNCTIONALIZATION; BR/D EXCHANGE; DEUTERIUM; PALLADIUM; ALKYNYLATION; STRATEGY; TRITIUM; DRUG;
D O I
10.1016/j.tetlet.2020.152807
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [41] Late-Stage Diversification of Biarylphosphines through Rhodium(I)-Catalyzed C-H Bond Alkenylation with Internal Alkynes
    Zhang, Zhuan
    Cordier, Marie
    Dixneuf, Pierre H.
    Soule, Jean-Francois
    ORGANIC LETTERS, 2020, 22 (15) : 5936 - 5940
  • [42] Bulky, spherical, and fluorinated anion BArF induces 'on-water' activity of silver salt for the hydration of terminal alkynes
    Saha, Sayantani
    Sarbajna, Abir
    Bera, Jitendra K.
    TETRAHEDRON LETTERS, 2014, 55 (08) : 1444 - 1447
  • [43] Late-stage deuteration of 13C-enriched substrates for T1 prolongation in hyperpolarized 13C MRI
    Taglang, Celine
    Korenchan, David E.
    von Morze, Cornelius
    Yu, Justin
    Najac, Chloe
    Wang, Sinan
    Blecha, Joseph E.
    Subramaniam, Sukumar
    Bok, Robert
    VanBrocklin, Henry F.
    Vigneron, Daniel B.
    Ronen, Sabrina M.
    Sriram, Renuka
    Kurhanewicz, John
    Wilson, David M.
    Flavell, Robert R.
    CHEMICAL COMMUNICATIONS, 2018, 54 (41) : 5233 - 5236
  • [44] Efficient and selective external activator-free cobalt catalyst for hydroboration of terminal alkynes enabled by BiPyPhos
    Li, Zheng
    Zhao, Jiangui
    Xue, Weichao
    Tang, Juan
    Li, Shun
    Ge, Yicen
    Xu, Jiaqi
    Zheng, Xueli
    Li, Ruixiang
    Chen, Hua
    Fu, Haiyan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (22) : 4455 - 4460
  • [45] Silver-Catalyzed Stereoselective trans Addition of 4-Hydroxycoumarins to Haloalkynes and Late-Stage Nitration
    Hong, Xianfang
    Ma, Fang
    Zha, Dandan
    Li, Hongji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (12) : 2552 - 2556
  • [46] Polymer-Supported Cu-Nanoparticle as an Efficient and Recyclable Catalyst for Oxidative Homocoupling of Terminal Alkynes
    Aziz, Sk Tarik
    Ul Islam, Rafique
    CATALYSIS LETTERS, 2018, 148 (01) : 205 - 213
  • [47] Efficient late-stage synthesis of quaternary phosphonium salts from organothianthrenium salts via photocatalysis
    Liu, Jun
    Feng, Zhaoyu
    Li, Hanxiang
    Yu, Zhengze
    Wang, Hongyu
    Tang, Bo
    CHEMICAL COMMUNICATIONS, 2024, 60 (66) : 8760 - 8763
  • [48] c-Jun N-terminal kinase activation by nitrobenzoxadiazoles leads to late-stage autophagy inhibition
    Camilla Palumbo
    Anastasia De Luca
    Nicola Rosato
    Mariantonietta Forgione
    Dante Rotili
    Anna Maria Caccuri
    Journal of Translational Medicine, 14
  • [49] c-Jun N-terminal kinase activation by nitrobenzoxadiazoles leads to late-stage autophagy inhibition
    Palumbo, Camilla
    De Luca, Anastasia
    Rosato, Nicola
    Forgione, Mariantonietta
    Rotili, Dante
    Caccuri, Anna Maria
    JOURNAL OF TRANSLATIONAL MEDICINE, 2016, 14
  • [50] Late-Stage C-H Deuteration of Organic Compounds via Ligand-Enabled Palladium-Catalyzed Hydrogen Isotope Exchange
    van Gemmeren, Manuel
    Beller, Matthias
    SYNLETT, 2024, 35 (19) : 2153 - 2154