Metal-Free Oxidative Carbon-Heteroatom Bond Formation Through C-H Bond Functionalization

被引:242
作者
Samanta, Rajarshi [1 ]
Matcha, Kiran [1 ]
Antonchick, Andrey P. [1 ]
机构
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany
关键词
Metal-free reactions; Green chemistry; Reaction mechanisms; Heterocycles; C-H functionalization; Hypervalent iodine; ONE-POT SYNTHESIS; HYPERVALENT IODINE(III) REAGENT; TRANSITION-METAL; HIGHLY EFFICIENT; INTERMOLECULAR AMINATION; N-ACYLAMINOPHTHALIMIDES; RADICAL AZIDONATION; CATALYZED SYNTHESIS; C(SP(3))-H BONDS; PRIMARY ALCOHOLS;
D O I
10.1002/ejoc.201300286
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct methods of carbon-heteroatom bond formation through functionalization of non-reactive C-H bonds represent an attractive approach to the synthesis of interesting products. This review focuses on the development of metal-free coupling methods for unactivated compounds under oxidative reaction conditions. The utility of these methods in syntheses of desired products and the mechanisms of their formation are discussed with numerous examples.
引用
收藏
页码:5769 / 5804
页数:36
相关论文
共 161 条
  • [91] A DDQ-promoted metal-free cross-coupling of 1,3-diarylpropynes with hydroxyl via Sp3 C-H bond activation to form C-O bond
    Mo, Hanjie
    Bao, Weiliang
    [J]. TETRAHEDRON, 2011, 67 (26) : 4793 - 4799
  • [92] Observations on the transition-metal catalysed oxidation of alkanes in trifluoroacetic acid: urea-hydrogen peroxide/TFA as a convenient method for the oxidation of unactivated C-H bonds
    Moody, CJ
    O'Connell, JL
    [J]. CHEMICAL COMMUNICATIONS, 2000, (14) : 1311 - 1312
  • [93] New perspectives for iodine (III) reagents in (hetero)biaryl coupling reactions
    Moreno, I
    Tellitu, I
    Herrero, MT
    SanMartín, R
    Domínguez, E
    [J]. CURRENT ORGANIC CHEMISTRY, 2002, 6 (15) : 1433 - 1452
  • [94] Facile oxidative conversion of alcohols to esters using molecular iodine
    Mori, N
    Togo, H
    [J]. TETRAHEDRON, 2005, 61 (24) : 5915 - 5925
  • [95] Reactivity in the formation of lactones from aromatic carboxylic acids with organohypervalent iodine compounds in the Suarez system
    Muraki, T
    Togo, H
    Yokoyama, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1713 - 1716
  • [96] Remote functionalization: Cyclic alkoxylation onto aromatic ring via radical pathway
    Muraki, T
    Togo, H
    Yokoyama, M
    [J]. TETRAHEDRON LETTERS, 1996, 37 (14) : 2441 - 2444
  • [97] Nagashima A, 2007, HETEROCYCLES, V74, P273
  • [98] Iodobenzene catalysed synthesis of spirofurans and benzopyrans by oxidative cyclisation of vinylogous esters
    Ngatimin, Marsewi
    Frey, Raphael
    Andrews, Cecily
    Lupton, David W.
    Hutt, Oliver E.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (42) : 11778 - 11780
  • [99] Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid
    Ochiai, Masahito
    Yamane, Shinichi
    Hoque, Md. Mahbubul
    Saito, Motomichi
    Miyamoto, Kazunori
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (43) : 5280 - 5282
  • [100] Highly Regioselective Amination of Unactivated Alkanes by Hypervalent Sulfonylimino-λ3-Bromane
    Ochiai, Masahito
    Miyamoto, Kazunori
    Kaneaki, Takao
    Hayashi, Satoko
    Nakanishi, Waro
    [J]. SCIENCE, 2011, 332 (6028) : 448 - 451