Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination

被引：218
|
作者：
Liang, Chungen
Robert-Pedlard, Fabien
Fruit, Corinne
Mueller, Paul
Dodd, Robert H.
Dauban, Philippe
机构：
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 28期
关键词：
amination; C-H insertion; hypervalent iodine; nitrenes; rhodium;
D O I：
10.1002/anie.200601248
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Successful matchmaking: The combination of a chiral nitrene precursor with a chiral rhodium(II) catalyst is the key factor that allows efficient intermolecular regioselective C-H amination. Good-to-excellent yields and excellent diastereoselectivities can be obtained with a stoichiometric amount of the C-H bond containing substrate. nttl = N-1,8-naphthoyl-tert-leucine. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：4641 / 4644
页数：4
相关论文
共 50 条
  • [1] N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H Amination reactions
    Huard, Kim
    Lebel, Helene
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (20) : 6222 - 6230
  • [2] Asymmetric Synthesis of Amines through Rhodium-Catalyzed C-H Amination with Sulfonimidoylnitrenes
    Darses, Benjamin
    Jarvis, Amanda G.
    Mafroud, Abdel-Kader
    Estenne-Bouhtou, Genevieve
    Dargazanli, Gihad
    Dauban, Philippe
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2079 - 2087
  • [3] Rhodium-Catalyzed Direct C-H Amination of Benzamides with Aryl Azides: A Synthetic Route to Diarylamines
    Ryu, Jaeyune
    Shin, Kwangmin
    Park, Sae Hume
    Kim, Ji Young
    Chang, Sukbok
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9904 - 9908
  • [4] Rhodium-Catalyzed C-H Alkynylation of Arenes at Room Temperature
    Feng, Chao
    Loh, Teck-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (10) : 2722 - 2726
  • [5] Rhodium-Catalyzed Directed Sulfenylation of Arene C-H Bonds
    Yang, Yaxi
    Hou, Wei
    Qin, Lihuai
    Du, Juanjuan
    Feng, Huijin
    Zhou, Bing
    Li, Yuanchao
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) : 416 - 420
  • [6] Rhodium-Catalyzed Electrooxidative C-H Olefination of Benzamides
    Zhang, Yan
    Struwe, Julia
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (35) : 15076 - 15080
  • [7] Rhodium-Catalyzed C-H Bond Arylation of Arenes
    Bouffard, Jean
    Itami, Kenichiro
    C-H ACTIVATION, 2010, 292 : 231 - 280
  • [8] Intermolecular C-H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates
    Yuan, Si-Wen
    Han, Hui
    Li, Yan-Lin
    Wu, Xueli
    Bao, Xiaoguang
    Gu, Zheng-Yang
    Xia, Ji-Bao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) : 8887 - 8892
  • [9] Rhodium-Catalyzed Oxidative Olefination of C-H Bonds in Acetophenones and Benzamides
    Patureau, Frederic W.
    Besset, Tatiana
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1064 - 1067
  • [10] Synthesis of 1,3-Diamines Through Rhodium-Catalyzed C-H Insertion
    Kurokawa, Toshiki
    Kim, Mihyong
    Du Bois, J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) : 2777 - 2779
12345