Selective Intermolecular Amination of C-H Bonds at Tertiary Carbon Centers

被引：114
|
作者：
Roizen, Jennifer L. [2 ]
Zalatan, David N. [1 ]
Du Bois, J. [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
[2] Duke Univ, Dept Chem, Durham, NC 27708 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 43期
基金：
美国国家科学基金会;
关键词：
amination; amines; C-H insertion; isotope effect; rhodium; MEMANTINE HYDROCHLORIDE; EFFICIENT SYNTHESIS; CATALYST; HYDROCARBONS; OXIDATION; POSITION; ALKANES; AZIDES;
D O I：
10.1002/anie.201304238
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
C-H insertion: A method for intermolecular amination of tertiary C-H bonds is described that uses limiting amounts of substrate and a convenient phenol-derived nitrogen source. Structure-selectivity and mechanistic studies suggest that steric interaction between the substrate and active oxidant is the principal determinant of product selectivity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：11343 / 11346
页数：4
相关论文
共 50 条
  • [1] Catalytic Intermolecular C(sp3)-H Amination: Selective Functionalization of Tertiary C-H Bonds vs Activated Benzylic C-H Bonds
    Brunard, Erwan
    Boquet, Vincent
    Van Elslande, Elsa
    Saget, Tanguy
    Dauban, Philippe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6407 - 6412
  • [2] Ritter-type amination of C-H bonds at tertiary carbon centers using iodic acid as an oxidant
    Kiyokawa, Kensuke
    Takemoto, Kenta
    Minakata, Satoshi
    CHEMICAL COMMUNICATIONS, 2016, 52 (89) : 13082 - 13085
  • [3] Computational Exploration of Dirhodium Complex-Catalyzed Selective Intermolecular Amination of Tertiary vs. Benzylic C-H Bonds
    Su, Xing-Xing
    Chen, Xia-He
    Ding, De-Bo
    She, Yuan-Bin
    Yang, Yun-Fang
    MOLECULES, 2023, 28 (04):
  • [4] Cu/Fe Catalyzed Intermolecular Oxidative Amination of Benzylic C-H Bonds
    Liu, Cong
    Zhang, Qi
    Li, Hongbo
    Guo, Shuangxi
    Xiao, Bin
    Deng, Wei
    Liu, Lei
    He, Wei
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (18) : 6208 - 6212
  • [5] Efficient diastereoselective intermolecular rhodium-catalyzed C-H amination
    Liang, Chungen
    Robert-Pedlard, Fabien
    Fruit, Corinne
    Mueller, Paul
    Dodd, Robert H.
    Dauban, Philippe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) : 4641 - 4644
  • [6] Advances in the Direct Amination of Azole C-H Bonds
    Zhang, Ming
    SYNTHESIS-STUTTGART, 2011, (21): : 3408 - 3417
  • [7] Stereoselective intermolecular C-H amination reactions
    Lebel, Helene
    Trudel, Carl
    Spitz, Cedric
    CHEMICAL COMMUNICATIONS, 2012, 48 (63) : 7799 - 7801
  • [8] Enantioselective Intermolecular Radical C-H Amination
    Jin, Li-Mei
    Xu, Pan
    Xie, Jingjing
    Zhang, X. Peter
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) : 20828 - 20836
  • [9] Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates
    Burman, Jacob S.
    Blakey, Simon B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) : 13666 - 13669
  • [10] Copper-Catalyzed Intermolecular Amination of Acidic Aryl C-H Bonds with Primary Aromatic Amines
    Zhao, Huaiqing
    Wang, Min
    Su, Weiping
    Hong, Maochun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1301 - 1306
12345