4.6 Article

Development of a Trimethylamine-Catalyzed Novel Synthesis of Azoxystrobin

Journal

ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 27, Issue 7, Pages 1276-1282

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.3c00033

Keywords

synthetic methodology; fungicide; azoxystrobin; trimethylamine; mechanistic study

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A novel method for the synthesis of Azoxystrobin using trimethylamine as a catalyst is reported in this study. The catalytic system offers several advantages including low cost, excellent reactivity, easy recovery, and minimal environmental impact. Mechanistic studies and DFT calculations suggest that the involvement of a highly active quaternary ammonium salt intermediate is responsible for the efficient catalysis.
We report the development of a novel method for the synthesisofAzoxystrobin, which employs trimethylamine as a catalyst. This appealingcatalytic system offers several advantages, including low cost, excellentreactivity, easy recovery, and the ability to be used repeatedly withminimal environmental impact. Mechanistic studies and density functionaltheory (DFT) calculations suggest that the involvement of a highlyactive quaternary ammonium salt intermediate is likely responsiblefor the efficient catalysis. This can be attributed to the low sterichindrance, flexible bare nature of the lone pair of electrons on thenitrogen atom, and low activation energy barrier of trimethylamine.These findings hold great promise for the mass production of Azoxystrobin.

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