Literature DB >> 30735304

Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry.

Dong Liu1, Hong-Xing Ma2, Ping Fang1, Tian-Sheng Mei1.   

Abstract

Transition-metal-catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition-metal-catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel-catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochemical cells.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  electrocatalysis; electrosynthesis; nickel; thiolation; thiyl radicals

Year:  2019        PMID: 30735304     DOI: 10.1002/anie.201900956

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


  11 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

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.  Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry.

Authors:  Chen Zhu; Huifeng Yue; Magnus Rueping
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

3.  Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.

Authors:  Zi-Qi Li; Wen-Ji He; Hui-Qi Ni; Keary M Engle
Journal:  Chem Sci       Date:  2022-05-02       Impact factor: 9.969

4.  Arylation of Axially Chiral Phosphorothioate Salts by Dinuclear PdI Catalysis.

Authors:  Xiang-Yu Chen; Maoping Pu; Hong-Gang Cheng; Theresa Sperger; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-09       Impact factor: 15.336

5.  Nickela-electrocatalyzed Mild C-H Alkylations at Room Temperature.

Authors:  Ramesh C Samanta; Julia Struwe; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 15.336

6.  Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates.

Authors:  Wei-Long Xing; De-Guang Liu; Ming-Chen Fu
Journal:  RSC Adv       Date:  2021-01-22       Impact factor: 3.361

7.  Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds.

Authors:  Lei Zhang; Xile Hu
Journal:  Chem Sci       Date:  2020-04-27       Impact factor: 9.825

8.  Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides.

Authors:  Weigang Zhang; Mengjun Huang; Zhenlei Zou; Zhengguang Wu; Shengyang Ni; Lingyu Kong; Youxuan Zheng; Yi Wang; Yi Pan
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825

9.  Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.

Authors:  Hai-Jun Zhang; Longrui Chen; Martins S Oderinde; Jacob T Edwards; Yu Kawamata; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-15       Impact factor: 16.823

10.  Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay.

Authors:  Shun Wang; Bei-Yi Cheng; Matea Sršen; Burkhard König
Journal:  J Am Chem Soc       Date:  2020-04-13       Impact factor: 15.419

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