Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with α-aryl-α-diazoesters

被引：75
作者：
Yu, Zhunzhun [1 ]
Li, Yongfeng [1 ]
Zhang, Peichao [1 ]
Liu, Lu [1 ]
Zhang, Junliang [1 ]
机构：
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China
来源：
CHEMICAL SCIENCE | 2019年 / 10卷 / 26期
基金：
中国国家自然科学基金;
关键词：
OXO GOLD CARBENES; ORGANIC-SYNTHESIS; DIAZO REAGENTS; SELECTIVE FUNCTIONALIZATION; QUATERNARY STEREOCENTERS; CATALYTIC DIVERGENT; INSERTION REACTIONS; 3+2 CYCLOADDITION; META; PHENOLS;
D O I：
10.1039/c9sc01657k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C-H bond functionalization of unprotected naphthols with alpha-aryl-alpha-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This protocol potentially provides a novel design for C-H bond functionalization.
引用
收藏
页码：6553 / 6559
页数：7
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共 127 条
  • [41] Modern Organic Synthesis with α-Diazocarbonyl Compounds
    Ford, Alan
    Miel, Hugues
    Ring, Aoife
    Slattery, Catherine N.
    Maguire, Anita R.
    McKervey, M. Anthony
    [J]. CHEMICAL REVIEWS, 2015, 115 (18) : 9981 - 10080
  • [42] Gold and diazo reagents: a fruitful tool for developing molecular complexity
    Fructos, Manuel R.
    Mar Diaz-Requejo, M.
    Perez, Pedro J.
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (46) : 7326 - 7335
  • [43] A gold catalyst for carbene-transfer reactions from ethyl diazoacetate
    Fructos, MR
    Belderrain, TR
    de Frémont, P
    Scott, NM
    Nolan, SP
    Díaz-Requejo, MM
    Pérez, PJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5284 - 5288
  • [44] From Understanding to Prediction: Gold- and Platinum-Based π-Acid Catalysis for Target Oriented Synthesis
    Fuerstner, Alois
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) : 925 - 938
  • [45] Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules
    Galloway, Warren R. J. D.
    Isidro-Llobet, Albert
    Spring, David R.
    [J]. NATURE COMMUNICATIONS, 2010, 1
  • [46] Enantioselective Palladium-Catalyzed C-H Functionalization of Indoles Using an Axially Chiral 2,2′-Bipyridine Ligand
    Gao, Xiang
    Wu, Bo
    Huang, Wen-Xue
    Chen, Mu-Wang
    Zhou, Yong-Gui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) : 11956 - 11960
  • [47] Gold-Containing and Gold-Generated 1,n-Dipoles as Useful Platforms toward Cycloadditions and Cyclizations
    Garayalde, David
    Nevado, Cristina
    [J]. ACS CATALYSIS, 2012, 2 (07): : 1462 - 1479
  • [48] Catalytic X-H insertion reactions based on carbenoids
    Gillingham, Dennis
    Fei, Na
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 4918 - 4931
  • [49] Three- and four-coordinate gold(I) complexes
    Gimeno, MC
    Laguna, A
    [J]. CHEMICAL REVIEWS, 1997, 97 (03) : 511 - 522
  • [50] Relativistic effects in homogeneous gold catalysis
    Gorin, David J.
    Toste, F. Dean
    [J]. NATURE, 2007, 446 (7134) : 395 - 403
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