Related Experiment Video
Updated: May 26, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Amination of Diaryl Sulfoxides with Amides
Chuntao Zhong1, Yanrong Ren1, Qiong Wu1
1School of Chemistry and Material Science, Jiangsu Normal University, Xuzhou 221116, China.
Abstract:
The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the amination reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reaction involves the activation of C-S and C-N bonds and the formation of a C-N bond with amides serving as amine surrogates. A broad range of sulfoxides and amides are compatible, furnishing substituted aniline in yields of up to 89%, and the protocol is scalable. Good regioselectivity was observed favoring the electron-deficient and less sterically hindered phenyl groups when unsymmetrical diphenyl sulfoxides were employed.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
