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Literature DB >> 22589147

Catalytic C-H amination with aromatic amines.

Raymond T Gephart¹, Daria L Huang, Mae Joanne B Aguila, Graham Schmidt, Andi Shahu, Timothy H Warren.

Abstract

Aniline joins the club: A β-diketiminato copper(I) catalyst enables C-H amination of anilines employing low catalyst loadings to preclude oxidation to the diazene ArN=NAr. Electron-poor anilines are particularly resistant towards diazene formation and participate in the amination of strong and unactivated C-H bonds. N-alkyl anilines also take part in C-H amination.

Entities: Chemical

Mesh：

Substances：
Amines
Carbon
Hydrogen

Year: 2012 PMID： 22589147 DOI： 10.1002/anie.201201921

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

10 in total

Review 1. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

2. Metal-Free Preparation of Cycloalkyl Aryl Sulfides via Di-tert-butyl Peroxide-Promoted Oxidative C(sp3)[BOND]H Bond Thiolation of Cycloalkanes.

Authors: Jincan Zhao; Hong Fang; Jianlin Han; Yi Pan; Guigen Li
Journal: Adv Synth Catal Date: 2014-08-10 Impact factor: 5.837

3. Late-Stage Intermolecular Allylic C-H Amination.

Authors: Takafumi Ide; Kaibo Feng; Charlie F Dixon; Dawei Teng; Joseph R Clark; Wei Han; Chloe I Wendell; Vanessa Koch; M Christina White
Journal: J Am Chem Soc Date: 2021-09-13 Impact factor: 15.419

4. Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

Authors: Pericles Stavropoulos
Journal: Comments Mod Chem A Comments Inorg Chem Date: 2016-04-29 Impact factor: 4.533

5. Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors: Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal: J Am Chem Soc Date: 2013-01-03 Impact factor: 15.419

6. Intermolecular CDC amination of remote and proximal unactivated C_sp³ -H bonds through intrinsic substrate reactivity - expanding towards a traceless directing group.

Authors: Suresh Rajamanickam; Mayank Saraswat; Sugumar Venkataramani; Bhisma K Patel
Journal: Chem Sci Date: 2021-10-27 Impact factor: 9.825

10. Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

Authors: Mong-Feng Chiou; Haigen Xiong; Yajun Li; Hongli Bao; Xinhao Zhang
Journal: Molecules Date: 2020-03-09 Impact factor: 4.411

10 in total

Catalytic C-H amination with aromatic amines.

Review 1. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

2. Metal-Free Preparation of Cycloalkyl Aryl Sulfides via Di-tert-butyl Peroxide-Promoted Oxidative C(sp3)[BOND]H Bond Thiolation of Cycloalkanes.

3. Late-Stage Intermolecular Allylic C-H Amination.

4. Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

5. Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

6. Intermolecular CDC amination of remote and proximal unactivated C_sp³ -H bonds through intrinsic substrate reactivity - expanding towards a traceless directing group.

7. Asymmetric radical carboesterification of dienes.

8. Copper(ii) ketimides in sp³ C-H amination.

9. Chemoselective single-site Earth-abundant metal catalysts at metal-organic framework nodes.

10. Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes.

Review 1. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 1. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.