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
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 26期
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
  • [11] Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur
    Chen, Chao
    Chu, Lingling
    Qing, Feng-Ling
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12454 - 12457
  • [12] Hypervalent iodine in synthesis. Part 54: One-step conversion of aryl aldehydes to aroyl azides using a combined reagent of (diacetoxyiodo)benzene with sodium azide
    Chen, DJ
    Chen, ZC
    [J]. TETRAHEDRON LETTERS, 2000, 41 (38) : 7361 - 7363
  • [13] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction
    Chen, Long
    Shi, Erbo
    Liu, Zhaojun
    Chen, Shulin
    Wei, Wei
    Li, Hong
    Xu, Kai
    Wan, Xiaobing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4085 - 4089
  • [14] Chen X., 2009, ANGEW CHEM, V121, P5196
  • [15] 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
  • [16] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions
    Cho, Seung Hwan
    Yoon, Jungho
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5996 - 6005
  • [17] An Intramolecular PIFA-Mediated Metal-Free Allylic Oxycarbonylation Reaction and Its Application to the Preparation of Furopyrimidinones
    Couto, Irantzu
    Tellitu, Imanol
    Dominguez, Esther
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) : 7954 - 7957
  • [18] Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis
    De Sarkar, Suman
    Studer, Armido
    [J]. ORGANIC LETTERS, 2010, 12 (09) : 1992 - 1995
  • [19] SYNTHESIS OF CULARINE AND SARCOCAPNINE VIA ENIUM IONS AND A NEW, HIGHLY DIASTEREOSELECTIVE REDUCTIVE METHYLATION
    DESOUSA, JDF
    RODRIGUES, JAR
    ABRAMOVITCH, RA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) : 9745 - 9746
  • [20] Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
    Dohi, Toshifumi
    Ito, Motoki
    Yamaoka, Nobutaka
    Morimoto, Koji
    Fujioka, Hiromichi
    Kita, Yasuyuki
    [J]. TETRAHEDRON, 2009, 65 (52) : 10797 - 10815
12345678910