An Easy and Adjustable One-Pot Access to Pheromonal Blends of Fall Armyworm (Spodoptera frugiperda) Relying on a Key Ligand- and Additive-Free Iron-Catalyzed Cross-Coupling

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2024-04-23 DOI:10.1021/acs.oprd.4c00034

Pablo Chourreu, Olivier Guerret, Eric Gayon* and Guillaume Lefèvre*,

引用次数: 0

Abstract

We describe in this report a convenient convergent synthesis of the pheromonal blend of Spodoptera frugiperda, relying on a key ligand- and additive-free iron-catalyzed cross-coupling, operating at a low 0.1 mol % catalytic charge. This approach relies on the use of the same electrophilic partner for the preparation of the three components of the blend, which can be prepared altogether in a single step in 94% isolated yield. Overall, the pheromonal blend is obtained with a 61% yield at a 20 g scale, with accurate control of the distribution of its three components.

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利用关键配体和无添加剂铁催化交叉偶联技术，轻松实现可调节的一锅式秋陆虫（Spodoptera frugiperda）信息素混合物获取途径

在本报告中，我们介绍了一种便捷的蛙类蚜虫信息素混合物的聚合合成方法，该方法依赖于一种关键配体和无添加剂的铁催化交叉偶联，在 0.1 摩尔 % 的低催化电荷下运行。这种方法依赖于使用相同的亲电伙伴来制备混合物的三种成分，只需一个步骤即可制备完毕，分离收率高达 94%。总之，在精确控制三种成分分布的情况下，以 20 克的规模制备的费洛蒙混合物的收率为 61%。

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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.