Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

被引:3
作者
Li, Weipiao [1 ,2 ]
Gao, Jiajun [1 ,2 ]
Mao, Ting [1 ,2 ]
Li, Xuefei [3 ]
Wang, An-Jun [2 ]
Wang, Pan [1 ]
Wang, Hao-Yang [2 ,4 ]
He, Chun-Yang [1 ,2 ]
机构
[1] Zunyi Med Univ, Affiliated Hosp Zunyi Med Univ, Dept Nucl Med, Zunyi 563000, Guizhou, Peoples R China
[2] Zunyi Med Univ, Gener Drug Res Ctr Guizhou Prov, Key Lab Biocatalysis & Chiral Drug Synth Guizhou P, Zunyi 563000, Guizhou, Peoples R China
[3] United Imaging Healthcare Grp Co Ltd, Cent Res Inst, Shanghai 201800, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
trifluoromethyl boronic esters; electron donor-acceptor complex; visible light induced; alkylation; QUATERNARY CARBONS; CONSTRUCTION; CF3;
D O I
10.1002/adsc.202300133
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We demonstrated a practical and general methodology for the synthesis of secondary trifluoromethyl boronic esters through visible light induced decarboxylative alkylation reaction. This reaction was driven by the photochemical activity of electron donor-acceptor (EDA) complex. Except for wide group tolerance, moderate to high yields and simple reaction conditions, the practicality of this protocol was further demonstrated by direct modification of bioactive molecules and further derivations.
引用
收藏
页码:1596 / 1601
页数:6
相关论文
共 36 条
  • [1] Synthesis and Applications of α-Trifluoromethylated Alkylboron Compounds
    Argintaru, O. Andreea
    Ryu, DaWeon
    Aron, Ioana
    Molander, Gary A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) : 13656 - 13660
  • [2] Quantification of Boron Compound Concentration for BNCT Using Positron Emission Tomography
    Balcerzyk, Marcin
    De-Miguel, Manuel
    Guerrero, Carlos
    Fernandez, Begona
    [J]. CELLS, 2020, 9 (09) : 1 - 11
  • [3] Dual Catalytic Strategy for Forging sp2-sp3 and sp3-sp3 Architectures via β-Scission of Aliphatic Alcohol Derivatives
    Cong, Fei
    Lv, Xin-Yang
    Day, Craig S.
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) : 20594 - 20599
  • [4] Preclinical profile of befloxatone, a new reversible MAO-A inhibitor
    Curet, O
    Damoiseau-Ovens, G
    Sauvage, C
    Sontag, N
    Avenet, P
    Depoortere, H
    Caille, D
    Bergis, O
    Scatton, B
    [J]. JOURNAL OF AFFECTIVE DISORDERS, 1998, 51 (03) : 287 - 303
  • [5] Nickel-Catalyzed Cross-Coupling of Amino-Acid-Derived Alkylzinc Reagents with Alkyl Bromides/Chlorides: Access to Diverse Unnatural Amino Acids
    Gou, Fei-Hu
    Ma, Ming-Jian
    Wang, An-Jun
    Zhao, Liang
    Wang, Haoyang
    Tong, Jie
    Wang, Ze
    Wang, Zhen
    He, Chun-Yang
    [J]. ORGANIC LETTERS, 2022, 24 (01) : 240 - 244
  • [6] Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor
    Guo, Peng
    Tao, Maoling
    Xu, Wen-Wen
    Wang, An-Jun
    Li, Weipiao
    Yao, Qiuli
    Tong, Jie
    He, Chun-Yang
    [J]. ORGANIC LETTERS, 2022, 24 (11) : 2143 - 2148
  • [7] The basis and advances in clinical application of boron neutron capture therapy
    He, Huifang
    Li, Jiyuan
    Jiang, Ping
    Tian, Suqing
    Wang, Hao
    Fan, Ruitai
    Liu, Junqi
    Yang, Yuyan
    Liu, Zhibo
    Wang, Junjie
    [J]. RADIATION ONCOLOGY, 2021, 16 (01)
  • [8] Herrmann K, 2020, LANCET ONCOL, V21, pE146, DOI 10.1016/S1470-2045(19)30821-6
  • [9] Prostate Cancer Theranostics: Concurrent Approvals by the Food and Drug Administration of the First Diagnostic Imaging Drug Indicated to Select Patients for a Paired Radioligand Therapeutic Drug
    Hofling, A. Alex
    Fotenos, Anthony F.
    Niu, Gang
    Fallah, Jaleh
    Agrawal, Sundeep
    Wang, Sue-Jane
    Marzella, Libero
    [J]. JOURNAL OF NUCLEAR MEDICINE, 2022, 63 (11) : 1642 - 1643
  • [10] A Biocatalytic Platform for Synthesis of Chiral α-Trifluoromethylated Organoborons
    Huang, Xiongyi
    Garcia-Borras, Marc
    Miao, Kun
    Kan, S. B. Jennifer
    Zutshi, Arjun
    Houk, K. N.
    Arnold, Frances H.
    [J]. ACS CENTRAL SCIENCE, 2019, 5 (02) : 270 - 276