C(sp3)-F, C(sp2)-F and C(sp3)-H bond activation at silicon(II) centers

被引：35
|
作者：
Swamy, V. S. V. S. N. [1 ,2 ]
Parvin, Nasrina [3 ]
Raj, K. Vipin [2 ,4 ]
Vanka, Kumar [2 ,4 ]
Sen, Sakya S. [1 ,2 ]
机构：
[1] CSIR, Natl Chem Lab, Inorgan Chem & Catalysis Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[2] Acad Sci & Innovat Res AcSIR, New Delhi 110020, India
[3] Indian Inst Sci Educ & Res, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[4] CSIR, Natl Chem Lab, Phys & Mat Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 71期
关键词：
C-F BOND; FLUORINATED BUILDING-BLOCKS; TRANSITION-METAL CENTERS; N-HETEROCYCLIC CARBENES; BORON TRIPLE BOND; PERFLUORINATED ARENES; SELECTIVE ACTIVATION; OXIDATIVE ADDITION; H ACTIVATION; KETONES;
D O I：
10.1039/c7cc05145j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Silylene [PhC(NtBu)(2)SiN(SiMe3)(2)] (1) cleaves the C(sp(3))-H and C-F bonds of acetophenone and 1,1,1-trifluoroacetophenone, respectively, under mild conditions. The reaction is initiated via a nucleophilic attack from the oxygen to the silicon atom followed by C-F/H bond cleavage. The scope of C-F bond activation has further been extended with C6F6 and C6F5CF3.
引用
收藏
页码：9850 / 9853
页数：4
相关论文
共 50 条
  • [21] Preparation of Alkyl Di(p-tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formations
    Higuchi, Kazuhiro
    Yamamoto, Kai
    Nakamura, Shunsuke
    Naruse, Haruka
    Ito, Motoki
    Sugiyama, Shigeo
    [J]. ORGANIC LETTERS, 2023, 25 (20) : 3766 - 3771
  • [22] Ethynyl-Directed Dual C(sp3)-H Activation Polymerization to Construct Regio- and Stereoregular C(sp3)-C(sp3) Bond Polymers
    Wang, Jia
    Li, Mingzhao
    Xu, Liguo
    Huang, Die
    Qin, Anjun
    Wang, Xin
    [J]. MACROMOLECULES, 2023, 57 (01) : 122 - 131
  • [23] Photochemical C-H bond coupling for (hetero)aryl C(sp2)-C(sp3) bond construction
    Zhao, Yating
    Xia, Wujiong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 4951 - 4963
  • [24] Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis
    Ociepa, Michal
    Turkowska, Joanna
    Gryko, Dorota
    [J]. ACS CATALYSIS, 2018, 8 (12): : 11362 - 11367
  • [25] Pd-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds
    Ali, Wajid
    Oliver, Gwyndaf A.
    Werz, Daniel B.
    Maiti, Debabrata
    [J]. CHEMICAL SOCIETY REVIEWS, 2024, 53 (19) : 9904 - 9953
  • [26] Chemoselective Activation of sp3 vs sp2 C-H Bonds with Pd(II)
    Curto, John M.
    Kozlowski, Marisa C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 18 - 21
  • [27] Rhodium(I)-Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion
    Xia, Ying
    Feng, Sheng
    Liu, Zhen
    Zhang, Yan
    Wang, Jianbo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7891 - 7894
  • [28] Direct oxidation of the C(sp2)-C(sp3) bond from benzyltrimethylsilanes to phenols
    Li, Wei
    Gao, Guolin
    Gao, Yuan
    Yang, Chao
    Xia, Wujiong
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (38) : 5291 - 5293
  • [29] Aminodealkenylation: Ozonolysis and copper catalysis convert C(sp3)-C(sp2) bonds to C(sp3)-N bonds
    He, Zhiqi
    Moreno, Jose Antonio
    Swain, Manisha
    Wu, Jason
    Kwon, Ohyun
    [J]. SCIENCE, 2023, 381 (6660) : 877 - 885
  • [30] Allylic C(sp3)-C(sp3) Bond Formation Through Pd-Catalyzed C(sp3)-H Activation of Alkenes and 1,4-Dienes
    Muzart, Jacques
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2268 - 2288
12345