Noncovalent Interaction in Transition Metal-Catalyzed Selective C-H Activation

被引:37
|
作者
Liao Gang [1 ]
Wu Yong-Jie [1 ]
Shi Bing-Feng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
noncovalent interaction; selectivity; C-H activation; transient directing group; TRANSIENT DIRECTING GROUPS; PLANAR CHIRAL FERROCENES; ENANTIOSELECTIVE SYNTHESIS; BOND ACTIVATION; BORYLATION; FUNCTIONALIZATION; LIGAND; ORGANOCATALYSIS;
D O I
10.6023/A20020027
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition metal-catalyzed direct C-H functionalization is one of the most efficient and powerful tools for the rapid synthesis of organic molecules. The use of functional groups in the molecules or covalently attached coordinating groups as directing groups has been realized as a major strategy to control the selectivity. Noncovalent interactions are of great importance in the field of molecular biology, supramolecular chemistry, material science and drug discovery. More recently, the use of well-designed ligands to enable the site-selective C-H functionalization via noncovalent interactions has emerged as a highly promising yet relatively less explored strategy. In this perspective, recent advances in this cutting-edge area are summarized. The perspective was classified into four sections according to the type of noncovalent interactions, including hydrogen bonding, ion pair, Lewis acid-base interaction and electrostatic interaction. Emphasis is placed on the mode of noncovalent interactions among the transition metals, ligands and substrates. The limitation of current research and the prospect of future work will also be discussed. We anticipate that this strategy might become a promising complementary strategy to control the positional selectivity in C-H functionalization reactions.
引用
收藏
页码:289 / 298
页数:10
相关论文
共 88 条
  • [1] Regiocontrolled Remote C-H Olefination of Small Heterocycles
    Achar, Tapas Kumar
    Ramakrishna, Kankanala
    Pal, Tapas
    Porey, Sandip
    Dolui, Pravas
    Biswas, Jyoti Prasad
    Maiti, Debabrata
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (68) : 17906 - 17910
  • [2] Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides
    Bai, Shao-Tao
    Bheeter, Charles B.
    Reek, Joost N. H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (37) : 13039 - 13043
  • [3] Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions
    Bastidas, Jose R. Montero
    Oleskey, Thomas J.
    Miller, Susanne L.
    Smith, Milton R., III
    Maleczka, Robert E., Jr.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (39) : 15483 - 15487
  • [4] Combining transition metals and transient directing groups for C-H functionalizations
    Bhattacharya, Trisha
    Pimparkar, Sandeep
    Maiti, Debabrata
    [J]. RSC ADVANCES, 2018, 8 (35) : 19456 - 19464
  • [5] Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides
    Bisht, Ranjana
    Hoque, Md Emdadul
    Chattopadhyay, Buddhadeb
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (48) : 15762 - 15766
  • [6] Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines
    Bisht, Ranjana
    Chattopadhyay, Buddhadeb
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) : 84 - 87
  • [7] Novel Noncovalent Interactions in Catalysis: A Focus on Halogen, Chalcogen, and Anion-π Bonding
    Breugst, Martin
    von der Heiden, Daniel
    Schmauck, Julie
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (15): : 3224 - 3236
  • [8] Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions
    Chattopadhyay, Buddhadeb
    Dannatt, Jonathan E.
    Andujar-De Sanctis, Ivonne L.
    Gore, Kristin A.
    Maleczka, Robert E., Jr.
    Singleton, Daniel A.
    Smith, Milton R., III
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7864 - 7871
  • [9] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [10] Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group
    Chen, Xiao-Yang
    Ozturk, Seyma
    Sorensen, Erik J.
    [J]. ORGANIC LETTERS, 2017, 19 (05) : 1140 - 1143