Literature DB >> 27726267

New Design of a Disulfurating Reagent: Facile and Straightforward Pathway to Unsymmetrical Disulfanes by Copper-Catalyzed Oxidative Cross-Coupling.

Xiao Xiao1, Minghao Feng1, Xuefeng Jiang2,3,4.   

Abstract

A novel reagent, which introduces two sulfur atoms in one step, was designed and used for the construction of diverse disulfanes by copper-catalyzed oxidative cross-coupling under mild reaction conditions. By applying this stable and readily prepared reagent, late-stage modification of pharmaceuticals and natural products can be achieved straightforward. The scaled-up experiments further indicated the practicality of this protocol. The pH value of the system plays a key role in achieving highly selective cleavage of the C-S bond instead of a S-S bond in the transformation.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cross-coupling; disulfuration; sulfur; synthetic methods

Year:  2016        PMID: 27726267     DOI: 10.1002/anie.201608011

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


  8 in total

1.  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

2.  Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy.

Authors:  Fei Wang; Ying Chen; Weidong Rao; Lutz Ackermann; Shun-Yi Wang
Journal:  Nat Commun       Date:  2022-05-11       Impact factor: 17.694

3.  Polysulfurating reagent design for unsymmetrical polysulfide construction.

Authors:  Xiao Xiao; Jiahui Xue; Xuefeng Jiang
Journal:  Nat Commun       Date:  2018-06-06       Impact factor: 14.919

4.  Design and application of α-ketothioesters as 1,2-dicarbonyl-forming reagents.

Authors:  Ming Wang; Zhihong Dai; Xuefeng Jiang
Journal:  Nat Commun       Date:  2019-06-17       Impact factor: 14.919

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.  A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes.

Authors:  Raju Jannapu Reddy; Md Waheed; Jangam Jagadesh Kumar
Journal:  RSC Adv       Date:  2018-12-04       Impact factor: 4.036

7.  Homocouplings of Sodium Arenesulfinates: Selective Access to Symmetric Diaryl Sulfides and Diaryl Disulfides.

Authors:  Xin-Zhang Yu; Wen-Long Wei; Yu-Lan Niu; Xing Li; Ming Wang; Wen-Chao Gao
Journal:  Molecules       Date:  2022-09-22       Impact factor: 4.927

8.  Electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes with hydrogen evolution.

Authors:  Yong Yuan; Yixuan Chen; Shan Tang; Zhiliang Huang; Aiwen Lei
Journal:  Sci Adv       Date:  2018-08-03       Impact factor: 14.136

  8 in total

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