B(C6F5)3-Catalyzed α-Deuteration of Bioactive Carbonyl Compounds with D2O

被引：24
|
作者：
Chang, Yejin [1 ]
Myers, Tanner [1 ]
Wasa, Masayuki [1 ]
机构：
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 02期
关键词：
Deuterated drug; Frustrated Lewis pair; Late-stage functionalization; Cooperative catalysis; HYDROLYTIC KINETIC RESOLUTION; ASYMMETRIC CATALYSIS; TERMINAL EPOXIDES; DRUG DISCOVERY; DEUTERIUM; EFFICIENT; TRITIUM; TRIS(PENTAFLUOROPHENYL)BORON; TRITIATION; COMPLEXES;
D O I：
10.1002/adsc.201901419
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient deuteration process of alpha-C-H bonds in various carbonyl-based pharmaceutical compounds has been developed. Catalytic reactions are initiated by the action of Lewis acidic B(C6F5)(3) and D2O, converting a drug molecule into the corresponding boron-enolate. Ensuing deuteration of the enolate by in situ-generated D2O+-H then results in the formation of alpha-deuterated bioactive carbonyl compounds with up to >98% deuterium incorporation.
引用
收藏
页码：360 / 364
页数：5
相关论文
共 50 条
  • [1] B(C6F5)3-Catalyzed Regioselective Deuteration of Electron-Rich Aromatic and Heteroaromatic Compounds
    Li, Wu
    Wang, Ming-Ming
    Hu, Yuya
    Werner, Thomas
    ORGANIC LETTERS, 2017, 19 (21) : 5768 - 5771
  • [2] B(C6F5)3-Catalyzed Intramolecular Hydroalkoxylation Deuteration Reactions of Unactivated Alkynyl Alcohols
    Tang, Jianbo
    Bai, Jian-Fei
    Zheng, Jinfeng
    Li, Shuangshuang
    Jiang, Zhi-Jiang
    Chen, Jia
    Gao, Kun
    Gao, Zhanghua
    ORGANIC LETTERS, 2023, 25 (37) : 6891 - 6896
  • [3] Modified Chemoselective Reduction and Consecutive Regioselective Deuteration Reaction Catalyzed by B(C6F5)3
    Park, Se Yeon
    Kim, Jaehwan
    Ko, Haye Min
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04) : 1996 - 2005
  • [4] B(C6F5)3-Catalyzed Synthesis of 3,3′-Bisindolylmethane Derivatives
    Ma, Jinyu
    Liu, Shuanglei
    Zhang, Zhenguo
    Jun, Junyang
    Jia, Zhenhua
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2020, 41 (10): : 2225 - 2229
  • [5] Organocatalyzed α-Deuteration of Ketones and Bioactive Carbonyl Compounds Using D2O as Deuterium Source
    Goyal, Pooja
    Dubey, Akhil K.
    Chowdhury, Raghunath
    CHEMISTRYSELECT, 2025, 10 (12):
  • [6] B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
    Basak, Shyam
    Alvarez-Montoya, Ana
    Winfrey, Laura
    Melen, Rebecca L.
    Morrill, Louis C.
    Pulis, Alexander P.
    ACS CATALYSIS, 2020, 10 (08): : 4835 - 4840
  • [7] B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines
    Shi, Lei
    Bao, Robert Li-Yuan
    Zheng, Limin
    Zhao, Rong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (38) : 6550 - 6556
  • [8] B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes: an approach toward bis(indolyl)alkanes
    Ling, Fei
    Xiao, Lian
    Fang, Lu
    Feng, Cong
    Xie, Zhen
    Lv, Yaping
    Zhong, Weihui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (47) : 9274 - 9278
  • [9] B(C6F5)3-Catalyzed C-Si/Si-H Cross-Metathesis of Hydrosilanes
    Ma, Yuanhong
    Zhang, Liang
    Luo, Yong
    Nishiura, Masayoshi
    Hou, Zhaomin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) : 12434 - 12437
  • [10] Interaction of Metal Oxido Compounds with B(C6F5)3
    Zwettler, Niklas
    Moesch-Zanetti, Nadia C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (24) : 6064 - 6076
12345