流动中电化学霍夫曼重排合成氨基甲酸酯的百克尺度

IF 3.5 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2025-08-12 DOI:10.1021/acs.oprd.5c00234

Darryl F. Nater, Rong Zhao, Johannes Rocker, Coline Boche, Dabeen Yun, Bernd Werner, Patrick Löb, Athanassios Ziogas and Siegfried R. Waldvogel*,

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引用次数: 0

摘要

烷基和芳基羧胺的霍夫曼重排可以在百图尺度上电化学实现。必要的卤素种类和碱等价物是由甲醇中的溴化钠通过电解产生的。载体电解质和溶剂都起到了介质、助电导剂和反应伙伴的作用。如果使用简单的玻璃碳阳极，这种电化学转换可以在简单的和商用的板框电池中进行。阳极表面面积为162 cm2，产率为104 mmol / h。

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Hectogram-Scale Synthesis of Carbamates Using Electrochemical Hofmann Rearrangement in Flow

The Hofmann rearrangement of alkyl and aryl carboxamides can be achieved electrochemically on a hectogram scale. The necessary halogen species and base equivalents are generated from sodium bromide in methanol by electrolysis. Both the supporting electrolyte and the solvent fulfill the role of mediator, conductivity-enabling agent, and reaction partners. This electrochemical conversion can be carried out in simple and commercially available plate-frame cells if a simple glassy carbon anode is used. A productivity of 104 mmol per h is obtained with 162 cm² of anode surface.

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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.