Activation of the Si-B Interelement Bond: Mechanism, Catalysis, and Synthesis

被引:336
|
作者
Oestreich, Martin [1 ]
Hartmann, Eduard [1 ]
Mewald, Marius [1 ]
机构
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
关键词
TRANSITION-METAL-COMPLEXES; CONJUGATE SILYL TRANSFER; BETA-HYDROXY KETONES; SILICON-BORON BONDS; C-C CLEAVAGE; REGIOSELECTIVE SILABORATION; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC SILICON; ASYMMETRIC-SYNTHESIS; TERMINAL ALKYNES;
D O I
10.1021/cr3003517
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Si-B (silicon-boron) chemistry has rapidly grown into an independent area of synthetic main group chemistry. The selective incorporation of both a silicon and a boron atom into an unsaturated molecule in a single synthetic operation is valuable as both newly formed functional groups are extraordinarily versatile linchpins for subsequent (mainly) C-C bond formation. Creative application of the transition metal-catalyzed Si-B bond activation to various classes of unsaturated compounds combined with subtle effects of the ligand or other additives provided unique regio- and diastereo divergent as well as regio and stereoselective accesses to difunctional building blocks. With copper as the transition metal, the net monofunctionalization resembles the chemistry of silicon-based cuprates catalytic in copper, and similar reactivity and selectivity are seen for several acceptors. As to asymmetric transformations, Si-B chemistry is superior to existing methods.
引用
收藏
页码:402 / 441
页数:40
相关论文
共 50 条
  • [1] Activation of the Si-B interelement bond related to catalysis
    Feng, Jian-Jun
    Mao, Wenbin
    Zhang, Liangliang
    Oestreich, Martin
    CHEMICAL SOCIETY REVIEWS, 2021, 50 (03) : 2010 - 2073
  • [2] Si-B bond activation in asymmetric Cu(I) and Rh(I) catalysis
    Hartmann, Eduard
    Oestreich, Martin
    CHIMICA OGGI-CHEMISTRY TODAY, 2011, 29 (05) : 34 - 36
  • [3] Copper(I)-Catalyzed Regioselective Propargylic Substitution Involving Si-B Bond Activation
    Vyas, Devendra J.
    Hazra, Chinmoy K.
    Oestreich, Martin
    ORGANIC LETTERS, 2011, 13 (16) : 4462 - 4465
  • [4] InSitu Generation of Silylzinc by Si-B Bond Activation Enabling Silylzincation and Silaboration of Terminal Alkynes
    Nagashima, Yuki
    Yukimori, Daiki
    Wang, Chao
    Uchiyama, Masanobu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) : 8053 - 8057
  • [5] Copper-Catalyzed Si-B Bond Activation in the Nucleophilic Substitution of Primary Aliphatic Triflates
    Scharfbier, Jonas
    Oestreich, Martin
    SYNLETT, 2016, 27 (08) : 1274 - 1276
  • [6] In Situ Generation of Silyl Anion Species through Si-B Bond Activation for the Concerted Nucleophilic Aromatic Substitution of Fluoroarenes
    Kojima, Kumiko
    Nagashima, Yuki
    Wang, Chao
    Uchiyama, Masanobu
    CHEMPLUSCHEM, 2019, 84 (03): : 277 - 280
  • [7] Copper-Catalyzed Si-B Bond Activation in Branched-Selective Allylic Substitution of Linear Allylic Chlorides
    Vyas, Devendra J.
    Oestreich, Martin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8513 - 8515
  • [8] Development of a bond-order type interatomic potential for Si-B systems
    Kumagai, T.
    Hara, S.
    Izumi, S.
    Sakai, S.
    MODELLING AND SIMULATION IN MATERIALS SCIENCE AND ENGINEERING, 2006, 14 (05) : S29 - S37
  • [9] INTERACTION IN THE SYSTEM SI-B
    ARABEI, BG
    INORGANIC MATERIALS, 1979, 15 (09) : 1251 - 1254
  • [10] Temperature and emissivity determination of Si-B materials by in-situ measurements: Application to catalysis
    Desportes, A
    Vervisch, P
    PROCEEDINGS OF THE FIFTH EUROPEAN SYMPOSIUM ON AEROTHERMODYNAMICS FOR SPACE VEHICLES, 2004, 563 : 69 - 74