Related Experiment Video
Updated: Aug 28, 2025

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
Published on: May 20, 2019
Ni-catalyzed C-S bond construction and cleavage
Su Huang1, Ming Wang1, Xuefeng Jiang1
1Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China. xfjiang@chem.ecnu.edu.cn.
Abstract:
Sulfur-containing compounds have attracted considerable interest due to their wide-ranging applications in pharmaceuticals, agriculture, natural products, and organic materials. The development of efficient and rapid methods for the construction and transformation of sulfur-containing compounds is of great importance. Since nickel is inexpensive and has a variety of valence states, strong nucleophilicity and low energy barriers for oxidative addition, the construction and transformation of sulfur-containing compounds by nickel-catalyzed cross-coupling have become important strategies. In addition, sulfur-containing compounds have also been playing increasingly important roles in the field of cross-coupling due to their thermodynamically stable but dynamic activity. This review will focus on nickel-catalyzed construction and transformation of various sulfide-containing compounds, such as sulfides, disulfides, and hypervalent sulfur-containing compounds.
Related Concept Videos
Alkynes to Carboxylic Acids: Oxidative Cleavage
Preparation and Reactions of Sulfides
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Radical Formation: Overview
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...

