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
  • [21] Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization
    Du, Yunfei
    Liu, Renhe
    Linn, Gregory
    Zhao, Kang
    [J]. ORGANIC LETTERS, 2006, 8 (26) : 5919 - 5922
  • [22] One-pot oxidative esterification and amidation of aldehydes
    Ekoue-Kovi, Kekeli
    Wolf, Christian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) : 6302 - 6315
  • [23] Metal-free one-pot oxidative amination of aldehydes to amides
    Ekoue-Kovi, Kekeli
    Wolf, Christian
    [J]. ORGANIC LETTERS, 2007, 9 (17) : 3429 - 3432
  • [24] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis
    Fache, F
    Schulz, E
    Tommasino, ML
    Lemaire, M
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2159 - 2231
  • [25] One-pot oxidative heteroannulations of N-sulfonylanilines with styrenes for the construction of 5-aminocoumaran derivatives
    Fan, Renhua
    Li, Weixun
    Ye, Yang
    Wang, Linfei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) : 1531 - 1536
  • [26] δ and α SP3 C-H bond oxidation of Sulfonamides with PhI(OAc)2/I2 under metal-free conditions
    Fan, Renhua
    Pu, Dongming
    Wen, Fengqi
    Wu, Jie
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) : 8994 - 8997
  • [27] Transition-Metal-Free Intermolecular Amination of sp3 C-H Bonds with Sulfonamides
    Fan, Renhua
    Li, Weixun
    Pu, Dongming
    Zhang, Li
    [J]. ORGANIC LETTERS, 2009, 11 (06) : 1425 - 1428
  • [28] Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry
    Feher, M
    Schmidt, JM
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2003, 43 (01): : 218 - 227
  • [29] A Metal-Free Oxidative Esterification of the Benzyl C?H Bond
    Feng, Jie
    Liang, Shuai
    Chen, Shan-Yong
    Zhang, Ji
    Fu, Song-Sen
    Yu, Xiao-Qi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (07) : 1287 - 1292
  • [30] A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes
    Froehr, Tanja
    Sindlinger, Christian P.
    Kloeckner, Ulrich
    Finkbeiner, Peter
    Nachtsheim, Boris J.
    [J]. ORGANIC LETTERS, 2011, 13 (14) : 3754 - 3757
12345678910