Literature DB >> 29740920

Electro-Oxidative S-H/S-H Cross-Coupling with Hydrogen Evolution: Facile Access to Unsymmetrical Disulfides.

Pengfei Huang1, Pan Wang1, Shan Tang1, Zhuangjiong Fu1, Aiwen Lei1,2.   

Abstract

Sulfur is an essential element because it exists widely in proteins. The disulfide bond is an important moiety in many different types of significant organic molecules. A new approach for oxidant- and catalyst-free S-H/S-H cross-coupling, with hydrogen evolution, to construct unsymmetrical disulfides was developed. Under the conditions of an undivided cell at room temperature, a series of unsymmetrical disulfides were prepared with up to 87 % yield from the direct coupling of an aryl mercaptan and alkyl mercaptan. Gram-scale synthesis also highlights the synthetic utility of this electrochemical strategy.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cross-coupling; electrochemistry; hydrogen; mercaptans; synthetic methods

Year:  2018        PMID: 29740920     DOI: 10.1002/anie.201803464

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


  8 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.  Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides.

Authors:  Jingjing Zhang; Armido Studer
Journal:  Nat Commun       Date:  2022-07-06       Impact factor: 17.694

3.  Stereoselective synthesis of sulfur-containing β-enaminonitrile derivatives through electrochemical Csp3-H bond oxidative functionalization of acetonitrile.

Authors:  Tian-Jun He; Zongren Ye; Zhuofeng Ke; Jing-Mei Huang
Journal:  Nat Commun       Date:  2019-02-19       Impact factor: 14.919

4.  Nickela-electrocatalyzed C-H Alkoxylation with Secondary Alcohols: Oxidation-Induced Reductive Elimination at Nickel(III).

Authors:  Shou-Kun Zhang; Julia Struwe; Lianrui Hu; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-16       Impact factor: 15.336

5.  Smart Flow Electrosynthesis and Application of Organodisulfides in Redox Flow Batteries.

Authors:  Qiliang Chen; Wei Guo; Yongzhu Fu
Journal:  Adv Sci (Weinh)       Date:  2021-11-10       Impact factor: 16.806

6.  tBuOK-triggered bond formation reactions.

Authors:  Yulong Xu; Xiaonan Shi; Lipeng Wu
Journal:  RSC Adv       Date:  2019-08-02       Impact factor: 3.361

7.  Alternating Current Electrolysis for the Electrocatalytic Synthesis of Mixed Disulfide via Sulfur-Sulfur Bond Metathesis towards Dynamic Disulfide Libraries.

Authors:  Lars Erik Sattler; Chris Josef Otten; Gerhard Hilt
Journal:  Chemistry       Date:  2020-02-18       Impact factor: 5.236

8.  Freeze the dynamicity: charge transfer complexation assisted control over the reaction pathway.

Authors:  Nilotpal Singha; Basab Kanti Das; Bapan Pramanik; Saurav Das; Debapratim Das
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825

  8 in total

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