Development of a Trimethylamine-Catalyzed Novel Synthesis of Azoxystrobin

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2023-06-16 DOI:10.1021/acs.oprd.3c00033

Binglian Yang, Wuping Xue, Baoqing Yu, Huailin Pang, Le Yu, Qingling Wang* and Dianhu Zhu*,

引用次数: 1

Abstract

We report the development of a novel method for the synthesis of Azoxystrobin, which employs trimethylamine as a catalyst. This appealing catalytic system offers several advantages, including low cost, excellent reactivity, easy recovery, and the ability to be used repeatedly with minimal environmental impact. Mechanistic studies and density functional theory (DFT) calculations suggest that the involvement of a highly active quaternary ammonium salt intermediate is likely responsible for the efficient catalysis. This can be attributed to the low steric hindrance, flexible bare nature of the lone pair of electrons on the nitrogen atom, and low activation energy barrier of trimethylamine. These findings hold great promise for the mass production of Azoxystrobin.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

三甲胺催化新合成偶氮嘧菌酯的研究

本文报道了一种以三甲胺为催化剂合成偶氮嘧菌酯的新方法。这种吸引人的催化系统具有几个优点，包括低成本，优异的反应性，易于回收，并且能够重复使用，对环境的影响最小。机理研究和密度泛函理论(DFT)计算表明，高活性季铵盐中间体的参与可能是有效催化的原因。这可归因于氮原子上的孤对电子的低空间位阻、柔性裸性质以及三甲胺的低活化能势垒。这些发现为氮氧嘧啶的大规模生产带来了巨大的希望。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.

期刊最新文献

Issue Publication Information Issue Editorial Masthead Practical, Large-Scale Preparation of Ni(tmeda)(o-tol)Cl Practical and Efficient Approach to Scalable Synthesis of Rucaparib Chemical and Biochemical Approaches to an Enantiomerically Pure 3,4-Disubstituted Tetrahydrofuran Derivative at a Multikilogram Scale: The Power of KRED