Tris(pentafluorophenyl)borane-Catalyzed Reactions Using Silanes

被引:39
|
作者
Hackel, Taylor [1 ]
McGrath, Nicholas A. [1 ]
机构
[1] Univ Wisconsin, Dept Chem & Biochem, La Crosse, WI 54601 USA
关键词
tris(pentafluorophenyl)borane; silane; carbonyl reduction; Lewis acid; Si-H activation; mechanism; stereoselective; METAL-FREE REDUCTION; FRUSTRATED LEWIS PAIRS; B(C6F5)(3)-CATALYZED HYDROSILYLATION; SELECTIVE REDUCTION; STEREOSELECTIVE HYDROSILYLATION; CARBONYL-COMPOUNDS; BORANE; ALCOHOLS; KETONES; HYDROSILATION;
D O I
10.3390/molecules24030432
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The utility of an electron-deficient, air stable, and commercially available Lewis acid tris(pentafluorophenyl)borane has recently been comprehensively explored. While being as reactive as its distant cousin boron trichloride, it has been shown to be much more stable and capable of catalyzing a variety of powerful transformations, even in the presence of water. The focus of this review will be to highlight those catalytic reactions that utilize a silane as a stoichiometric reductant in conjunction with tris(pentafluorophenyl) borane in the reduction of alcohols, carbonyls, or carbonyl-like derivatives.
引用
收藏
页数:30
相关论文
共 50 条
  • [41] Mechanism of Borane-Catalyzed Oligomerization of Arylallenes and Arylacetylenes
    Qu, Zheng-Wang
    Zhu, Hui
    Grimme, Stefan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (04)
  • [42] Complexation of tris(pentafluorophenyl)silanes with neutral Lewis bases
    Dilman, Alexander D.
    Levin, Vitalij V.
    Korlyukov, Alexander A.
    Belyakov, Pavel A.
    Struchkova, Marina I.
    Antipin, Mikhail Yu.
    Tartakovsky, Vladimir A.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (06) : 1005 - 1019
  • [43] Synthesis, Structure, and Stability of Adducts between Phosphide and Amide Anions and the Lewis Acids Borane, Tris(pentafluorophenyl)borane, and Tris(pentafluorophenyl)alane
    Fuller, Anna-Marie
    Mountford, Andrew J.
    Scott, Matthew L.
    Coles, Simon J.
    Horton, Peter N.
    Hughes, David L.
    Hursthouse, Michael B.
    Lancaster, Simon J.
    INORGANIC CHEMISTRY, 2009, 48 (23) : 11474 - 11482
  • [44] Borane-Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes to Tetrasubstituted Monofluoroalkenes
    He, Chunhu
    Zhou, Guoyi
    Yang, Guichun
    Wang, Feiyi
    Lu, Cuifen
    Nie, Junqi
    Ma, Chao
    ORGANIC LETTERS, 2024, 26 (26) : 5539 - 5543
  • [45] Pentamethylcyclopentadienylmethyltitanium Silsesquioxanes and Their Zwitterionic Complexes with Tris(pentafluorophenyl)borane
    Varga, Vojtech
    Pinkas, Jiri
    Cisarova, Ivana
    Horacek, Michal
    Mach, Karel
    ORGANOMETALLICS, 2009, 28 (24) : 6944 - 6956
  • [46] BORANE-CATALYZED CONDENSATION OF TRISILAZANE AND N-METHYLDISILAZANE
    SCANTLIN, WM
    NORMAN, AD
    INORGANIC CHEMISTRY, 1972, 11 (12) : 3082 - &
  • [47] Reaction of dimethylzirconocene with imidazole in the presence of tris(pentafluorophenyl)borane
    Rottger, D
    Erker, G
    Frohlich, R
    Kotila, S
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 518 (1-2) : 17 - 19
  • [48] Tris(pentafluorophenyl)borane catalyzed C-C and C-heteroatom bond formation
    Kumar, Gautam
    Roy, Sourav
    Chatterjee, Indranil
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (06) : 1230 - 1267
  • [49] Generation and characterization of the tris(pentafluorophenyl)borane radical anion
    Kwaan, RJ
    Harlan, CJ
    Norton, JR
    ORGANOMETALLICS, 2001, 20 (17) : 3818 - 3820
  • [50] Intermediates of tris(pentafluorophenyl)borane and dimethyl carbonate pave the way for deeper organosiloxane depolymerization reactions
    Protsak, Iryna
    Gun'ko, Volodymyr
    Morozov, Yevhenii
    Henderson, Ian M.
    Dong Zhang
    Zhang Yinjun
    Turov, Volodymyr
    POLYMER JOURNAL, 2021, 53 (04) : 573 - 579