Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C-C Bonds

被引:13
|
作者
Wang, Hao [1 ]
Ying, Ping [2 ]
Yu, Jingbo [1 ]
Su, Weike [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Hangzhou 310014, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China
基金
中国国家自然科学基金;
关键词
cross-dehydrogenative coupling; thermochemistry; photochemistry; electrochemistry; mechanochemistry; VISIBLE-LIGHT PHOTOREDOX; N-ARYL ENAMINES; H FUNCTIONALIZATION SYNTHESIS; HYDROGEN EVOLUTION REACTION; AMINO CARBONYL-COMPOUNDS; DIRECT ALPHA-ARYLATION; SOLVENT-FREE; TERTIARY-AMINES; PHENOL-ARENE; OXIDATIVE CYCLIZATION;
D O I
10.6023/cjoc202009053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cross-dehydrogenative coupling (CDC) reactions have been esteemed as one of the straightforward and efficient tool for C-C bond formation. Typically, these reactions are generally realized via solvent-based thermochemistry, using a round bottom flask and a magnetic or mechanical stirrer. With the development of new synthetic strategies, alternative technologies currently available in laboratories that facilitate CDC reactions, such as photochemistry, electrochemistry and mechanochemistry have arisen rapidly, providing green and high efficiency strategies for the construction of C-C bonds which are perfect complement to traditional thermochemistry. In order to compare the advantages of each approaches more clearly, and promote the development of CDC reactions, CDC reactions related to two or more enabling technologies of same or similar substrates are reviewed, hoping to provide help for the development of CDC reaction and the development of new organic synthesis methods.
引用
收藏
页码:1897 / 1924
页数:28
相关论文
共 144 条
  • [81] Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst
    Obst, Martin
    Koenig, Burkhard
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2358 - 2363
  • [82] Dehydrogenative coupling reactions catalysed by Rose Bengal using visible light irradiation
    Pan, Yuanhang
    Kee, Choon Wee
    Chen, Li
    Tan, Choon-Hong
    [J]. GREEN CHEMISTRY, 2011, 13 (10) : 2682 - 2685
  • [83] Metal-Free Cross-Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions
    Parvatkar, Prakash T.
    Manetsch, Roman
    Banik, Bimal K.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (01) : 6 - 30
  • [84] Efficient merging of copper and photoredox catalysis for the asymmetric cross-dehydrogenative-coupling of alkynes and tetrahydroisoquinolines
    Perepichka, Inna
    Kundu, Soumen
    Hearne, Zoe
    Li, Chao-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (02) : 447 - 451
  • [85] A diiodo-BODIPY postmodified metal-organic framework for efficient heterogeneous organo-photocatalysis
    Quan, Ying
    Li, Qiu-Yan
    Zhang, Quan
    Zhang, Wen-Qiang
    Lu, Han
    Yu, Jun-Hao
    Chen, Jian
    Zhao, Xinsheng
    Wang, Xiao-Jun
    [J]. RSC ADVANCES, 2016, 6 (29) : 23995 - 23999
  • [86] Copper (I) Catalyzed Sp3 C-H Arylation of N-Arylglycine Ester Derivatives under Aerobic Conditions
    Ramana, Daggupati V.
    Chowhan, L. Raju
    Chandrasekharam, Malapaka
    [J]. CHEMISTRYSELECT, 2017, 2 (07): : 2241 - 2244
  • [87] Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid CB2 receptor
    Reux, Bastien
    Nevalainen, Tapio
    Raitio, Katri H.
    Koskinen, Ari M. P.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (13) : 4441 - 4447
  • [88] Visible Light-Induced C-H Bond Functionalization: A Critical Review
    Revathi, Lekkala
    Ravindar, Lekkala
    Fang, Wan-Yin
    Rakesh, K. P.
    Qin, Hua-Li
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4652 - 4698
  • [89] Solvent-free carbon-carbon bond formations in ball mills
    Rodriguez, Beln
    Bruckmann, Angelika
    Rantanen, Toni
    Bolm, Carsten
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) : 2213 - 2233
  • [90] Dehydrogenative Anodic C-C Coupling of Phenols Bearing Electron-Withdrawing Groups
    Roeckl, Johannes L.
    Schollmeyer, Dieter
    Franke, Robert
    Waldvogel, Siegfried R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (01) : 315 - 319