微胶囊驱动的水中霍夫曼重排

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2024-06-28 DOI:10.1021/acs.oprd.4c00197

Xiaoqi Xing, Kangming Zhao, Zhidong Li, Ning Ye, Nan Zhao, Fengfeng Guo, Chunhua Qiao, Guoqiang Xu, Michael Parmentier, Fabrice Gallou, Bin Wu

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引用次数: 0

摘要

我们开发出了一种环境可持续的霍夫曼重排方法。与使用大量有机溶剂的传统方法相比，纳米蜂窝的存在使得这种转化在温和的条件下顺利进行，水是唯一的反应介质。在这些条件下，我们制备出了多种含有官能团的酰胺，并以良好甚至极高的收率（高达 99%）获得了复合胺产品。该工艺的规模已经扩大，并被证明可用于合成药物相关化合物。

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Micelle-Enabled Hofmann Rearrangement in Water

An environmentally sustainable approach for the Hofmann rearrangement was developed. The presence of nanomicelles allows such a transformation to proceed smoothly in mild conditions with water as the sole reaction medium compared to traditional methods, which use significant amounts of organic solvents. A variety of amides containing functional groups have been constructed under these conditions, affording the compounding amine product in good to excellent yields (up to 99%). The process was scaled up and proven to be robust for its implementation in the synthesis of pharmaceutically relevant compounds.

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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.