Literature DB >> 30664331

Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane.

Yujie Liang1, Fengguirong Lin1, Yeerlan Adeli1, Rui Jin1, Ning Jiao1,2.   

Abstract

Although the application of 1,2-dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C-H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value-added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late-stage chlorination of bioactive molecules.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; chlorination; dehydrochlorination; electrochemistry; radicals

Year:  2019        PMID: 30664331     DOI: 10.1002/anie.201814570

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


  10 in total

1.  Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach.

Authors:  Xiaohan Ye; Pengyi Zhao; Shuyao Zhang; Yanbin Zhang; Qilin Wang; Chuan Shan; Lukasz Wojtas; Hao Guo; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-04       Impact factor: 15.336

2.  Selective Halogenation of Pyridines Using Designed Phosphine Reagents.

Authors:  Jeffrey N Levy; Juan V Alegre-Requena; Renrong Liu; Robert S Paton; Andrew McNally
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3.  Ruthenaelectro-catalyzed C-H acyloxylation for late-stage tyrosine and oligopeptide diversification.

Authors:  Xiaoyan Hou; Nikolaos Kaplaneris; Binbin Yuan; Johanna Frey; Tsuyoshi Ohyama; Antonis M Messinis; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

4.  Distal Ruthenaelectro-Catalyzed meta-C-H Bromination with Aqueous HBr.

Authors:  Yulei Wang; Hendrik Simon; Xinran Chen; Zhipeng Lin; Shan Chen; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-16       Impact factor: 16.823

Review 5.  Recent advances in metal catalyst- and oxidant-free electrochemical C-H bond functionalization of nitrogen-containing heterocycles.

Authors:  Ya-Nan Li; Bin Wang; Ye-Kai Huang; Jin-Song Hu; Jia-Nan Sun
Journal:  Front Chem       Date:  2022-08-19       Impact factor: 5.545

Review 6.  Nanoscale zerovalent copper (nZVC) catalyzed environmental remediation of organic and inorganic contaminants: A review.

Authors:  Sandeep Kumar; Parminder Kaur; Ravinderdeep Singh Brar; J Nagendra Babu
Journal:  Heliyon       Date:  2022-08-08

7.  Photo-Induced Halogen-Atom Transfer: Generation of Halide Radicals for Selective Hydrohalogenation Reactions.

Authors:  Lilian Geniller; Marc Taillefer; Florian Jaroschik; Alexis Prieto
Journal:  Chemistry       Date:  2022-06-13       Impact factor: 5.020

8.  Electrocatalytic redox neutral [3 + 2] annulation of N-cyclopropylanilines and alkenes.

Authors:  Qi Wang; Qile Wang; Yuexiang Zhang; Yasmine M Mohamed; Carlos Pacheco; Nan Zheng; Richard N Zare; Hao Chen
Journal:  Chem Sci       Date:  2020-11-09       Impact factor: 9.825

9.  Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition.

Authors:  Zhuang Ma; Helin Lu; Ke Liao; Zhilong Chen
Journal:  iScience       Date:  2020-04-18

10.  Metalloenzyme-Inspired Ce-MOF Catalyst for Oxidative Halogenation Reactions.

Authors:  Sergio Rojas-Buzo; Patricia Concepción; José Luis Olloqui-Sariego; Manuel Moliner; Avelino Corma
Journal:  ACS Appl Mater Interfaces       Date:  2021-06-27       Impact factor: 10.383

  10 in total

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