ppm level Pd catalytic Suzuki-Miyaura coupling reaction in water and its application in the synthesis of Bixafen

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-01-17 DOI:10.1016/j.tet.2025.134464

Zhiyong Tan , Tingting Chen , Jiayi Shen , Wenjun Luo , Daohong Yu , Jinbin Zhu , Minjie Zhang , Weihong Zhong , Wei Guo

引用次数: 0

Abstract

We have developed a Pd-catalyzed Suzuki-Miyaura cross-coupling reaction for synthesizing key scaffold of important fungicides in water. The Pd-loading was as low as 30 ppm after optimization of experiment conditions with high TON. Additionally, the green, cheap and convenient ethanolamine was found to be as a highly efficient ligand for this transformation. Different heteroarylboronic halides and arylboronic acids were all suitable for construction of biphenyl scaffolds up to 98 % yield. We successfully carried out gram-scale experiments in two-step synthesis of Bixafen, making it a promising and environmental-friendly approach for industrialization.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.