Heterogeneous gold-catalyzed Sandmeyer coupling of aryldiazonium salts with sodium bromide or thiols for constructing C-Br and C-S bonds
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Updated: Jul 24, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
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.
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