Literature DB >> 29498166

Electrochemical Oxidative C-H Amination of Phenols: Access to Triarylamine Derivatives.

Shan Tang1, Siyuan Wang1, Yichang Liu1, Hengjiang Cong1, Aiwen Lei1,2.   

Abstract

Dehydrogenative C-H/N-H cross-coupling serves as one of the most straightforward and atom-economical approaches for C-N bond formation. In this work, an electrochemical reaction protocol has been developed for the oxidative C-H amination of unprotected phenols under undivided electrolytic conditions. Neither metal catalysts nor chemical oxidants are needed to facilitate the dehydrogenation process. A series of triarylamine derivatives could be obtained with good functional-group tolerance. The electrolysis is scalable and can be performed at ambient conditions.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; amination; cross-coupling; electrochemistry; heterocyles

Year:  2018        PMID: 29498166     DOI: 10.1002/anie.201800240

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


  16 in total

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Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Catalytic Oxidative Coupling of Phenols and Related Compounds.

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3.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors:  Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-18       Impact factor: 15.336

4.  Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C-H Aminations and Alkyl Deconstructive Carbofunctionalization.

Authors:  Taoyuan Liang; He Zhao; Lingzhen Gong; Huanfeng Jiang; Min Zhang
Journal:  iScience       Date:  2019-04-19

5.  Electrochemical Oxidative Clean Halogenation Using HX/NaX with Hydrogen Evolution.

Authors:  Yong Yuan; Anjin Yao; Yongfu Zheng; Meng Gao; Zhilin Zhou; Jin Qiao; Jiajia Hu; Baoqin Ye; Jing Zhao; Huilai Wen; Aiwen Lei
Journal:  iScience       Date:  2019-01-23

6.  Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

Authors:  Kun Liu; Shan Tang; Ting Wu; Shengchun Wang; Minzhu Zou; Hengjiang Cong; Aiwen Lei
Journal:  Nat Commun       Date:  2019-02-07       Impact factor: 14.919

7.  HBF4- and AgBF4-Catalyzed ortho-Alkylation of Diarylamines and Phenols.

Authors:  Christian K Rank; Bünyamin Özkaya; Frederic W Patureau
Journal:  Org Lett       Date:  2019-08-20       Impact factor: 6.005

8.  Mechanism of the Dehydrogenative Phenothiazination of Phenols.

Authors:  Monalisa Goswami; Alexander Konkel; Maryam Rahimi; Marie-Laure Louillat-Habermeyer; Harald Kelm; Rongwei Jin; Bas de Bruin; Frederic W Patureau
Journal:  Chemistry       Date:  2018-07-25       Impact factor: 5.236

9.  Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules.

Authors:  Chunlan Song; Kun Liu; Zhongjie Wang; Bo Ding; Shengchun Wang; Yue Weng; Chien-Wei Chiang; Aiwen Lei
Journal:  Chem Sci       Date:  2019-07-08       Impact factor: 9.825

10.  Visible Light Induced Metal-Free Carbene N-Carbazolation.

Authors:  Claire Empel; Frederic W Patureau; Rene M Koenigs
Journal:  J Org Chem       Date:  2019-08-15       Impact factor: 4.354

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