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

被引：115
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 51 条
[31]   Evidence for a One-Electron Mechanistic Regime in Dirhodium-Catalyzed Intermolecular C-H Amination [J].
Kornecki, Katherine P. ;
Berry, John F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) :5827-5832
[32]  
Lebel H., 2011, Catalyzed Carbon-Heteroatom Bond Formation, P137
[33]   Intermolecular C-H Amination of Complex Molecules: Insights into the Factors Governing the Selectivity [J].
Lescot, Camille ;
Darses, Benjamin ;
Collet, Florence ;
Retailleau, Pascal ;
Dauban, Philippe .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7232-7240
[34]   Imido transfer from bis(imido)ruthenium(VI) porphyrins to hydrocarbons: Effect of imido substituents, C-H bond dissociation energies, and RUVIN reduction potentials [J].
Leung, SKY ;
Tsui, WM ;
Huang, JS ;
Che, CM ;
Liang, JL ;
Zhu, NY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16629-16640
[35]   Toward a synthetically useful stereoselective C-H amination of hydrocarbons [J].
Liang, Chungen ;
Collet, Florence ;
Robert-Peillard, Fabien ;
Mueller, Paul ;
Dodd, Robert H. ;
Dauban, Philippe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :343-350
[36]   [FeIII(F20-tpp)Cl] Is an Effective Catalyst for Nitrene Transfer Reactions and Amination of Saturated Hydrocarbons with Sulfonyl and Aryl Azides as Nitrogen Source under Thermal and Microwave-Assisted Conditions [J].
Liu, Yungen ;
Che, Chi-Ming .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (34) :10494-10501
[37]  
Luo Y.-R., COMPREHENSIVE HDB CH, P19
[38]   New synthetic approach to Memantine hydrochloride starting from 1,3-dimethyl-adamantane [J].
Madhra, Mukesh K. ;
Sharma, Mukesh ;
Khanduri, C. H. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (05) :922-923
[39]   OXIDATIONS BY METHYL(TRIFLUOROMETHYL)DIOXIRANE .2. OXYFUNCTIONALIZATION OF SATURATED-HYDROCARBONS [J].
MELLO, R ;
FIORENTINO, M ;
FUSCO, C ;
CURCI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6749-6757
[40]   Rhodium(II)-catalyzed CH insertions with {[(4-nitrophenyl)sulfonyl]imino}phenyl-lambda(3)-iodane [J].
Nageli, I ;
Baud, C ;
Bernardinelli, G ;
Jacquier, Y ;
Moran, M ;
Muller, P .
HELVETICA CHIMICA ACTA, 1997, 80 (04) :1087-1105
123456