Related Experiment Video
Updated: Jul 24, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Heterogeneous gold-catalyzed Sandmeyer coupling of aryldiazonium salts with sodium bromide or thiols for constructing
Jiajia Li1, Jiajun Zeng1, Wenyan Hao1
1Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China. wenyanhao@jxnu.edu.cn.
Abstract:
An efficient heterogeneous gold-catalyzed Sandmeyer coupling of aryldiazonium salts with sodium bromide or thiols for the formation of C-Br and C-S bonds has been achieved in high yields and selectivities under mild conditions by using a bis(diphenylphosphinomethyl)amino-modified mesoporous MCM-41-immobilized gold(I) chloride complex [MCM-41-2Ph2PAuCl] as the catalyst without using sacrificial oxidants. Vital to the success of this C-heteroatom coupling is the nucleophile-promoted activation of aryldiazonium salts, which can serve as an efficient oxidant for the conversion of Au(I) to Au(III) without the use of a photocatalyst or an assisting ligand. This new heterogenized gold(I) complex can be easily prepared by a simple procedure and recovered via centrifugation, and recycled more than seven times without any significant loss of its catalytic efficiency.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Preparation of Nitriles
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction