Substituent Effects in NHC-Boranes: Reactivity Switch in the Nucleophilic Fluorination of NHC-Boranes

被引：5
|
作者：
Brahmi, Malika Makhlouf [1 ]
Malacria, Max [1 ]
Curran, Dennis P. [2 ]
Fensterbank, Louis [1 ]
Lacote, Emmanuel [1 ,3 ]
机构：
[1] Univ Paris 06, IPCM UMR 7201, F-75005 Paris, France
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[3] Univ Lyon 1, Inst Chim Lyon, UMR CNRS 5265, ESCPE Lyon, F-69616 Villeurbanne, France
来源：
SYNLETT | 2013年 / 24卷 / 10期
基金：
美国国家科学基金会;
关键词：
boron; carbene complexes; fluorine; cations; Lewis acids; LEWIS-ACID; BORENIUM; ACTIVATION; COMPLEXES; BORONIUM; IONS;
D O I：
10.1055/s-0033-1338847
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Substituents on the boron atom of NHC-boranes direct the reactivity of the ligated boreniums obtained through hydride abstraction. Depending on the electronics of the substituent, the reaction is selectively steered toward either B-substitution or Lewis base exchange.
引用
收藏
页码：1260 / 1262
页数：3
相关论文
共 48 条
  • [1] Chemistry of NHC-boranes
    Lacote, Emmanuel
    Curran, Dennis P.
    Fensterbank, Louis
    Malacria, Max
    Brahmi, Malika Makhlouf
    Solovyev, Andrey
    Monot, Julien
    Bonin-Dubarle, Helene
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [2] Thiolation of NHC-boranes: influence of the substitution at boron
    Vallet, Anne-Laure
    Lacote, Emmanuel
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (17) : 4234 - 4237
  • [3] Reactions of NHC-Boranes with Dibenzoyl Peroxide and Benzoic Acid
    Bolt, Daniel A.
    Curran, Dennis P.
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (11) : 2238 - 2244
  • [4] Photocatalytic C-F Bond Borylation of Polyfluoroarenes with NHC-boranes
    Xia, Peng-Ju
    Ye, Zhi-Peng
    Hu, Yuan-Zhuo
    Xiao, Jun -An
    Chen, Kai
    Xiang, Hao-Yue
    Chen, Xiao-Qing
    Yang, Hua
    ORGANIC LETTERS, 2020, 22 (05) : 1742 - 1747
  • [5] Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom
    Aupic, Clara
    Mohamed, Amel Abdou
    Figliola, Carlotta
    Nava, Paola
    Tuccio, Beatrice
    Chouraqui, Gaelle
    Parrain, Jean-Luc
    Chuzel, Olivier
    CHEMICAL SCIENCE, 2019, 10 (26) : 6524 - 6530
  • [6] Photoredox radical borylation of electron-deficient alkenes with NHC-boranes
    Zhu, Congjun
    Gao, Shan
    Li, Weipeng
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2020, 56 (100) : 15647 - 15650
  • [7] Visible-Light-Promoted Regioselective Hydroborylation of Ketene Dithioacetals with NHC-Boranes
    An, Yuanyuan
    Li, Xiaolong
    Xia, Shuangshuang
    Jian, Yongchan
    Wen, Fei
    Liu, Zhenyu
    He, Jiaying
    Shen, Yali
    Wang, Yubin
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21): : 15151 - 15158
  • [8] Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light
    Kawamoto, Takuji
    Morioka, Tsubasa
    Noguchi, Kohki
    Curran, Dennis P.
    Kamimura, Akio
    ORGANIC LETTERS, 2021, 23 (05) : 1825 - 1828
  • [9] Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC-boranes
    Zheng, Huitao
    Xiong, Honggang
    Su, Chaobo
    Cao, Hua
    Yao, Huagang
    Liu, Xiang
    RSC ADVANCES, 2021, 12 (01) : 470 - 474
  • [10] Photoredox-Controlled β-Regioselective Radical Hydroboration of Activated Alkenes with NHC-Boranes
    Zhu, Congjun
    Dong, Jie
    Liu, Xueting
    Gao, Liuzhou
    Zhao, Yue
    Xie, Jin
    Li, Shuhua
    Zhu, Chengjian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) : 12817 - 12821
12345