A Scalable Flow Electrolysis of Heterogeneous Mixtures Using a Rotating Cylinder Electrode Reactor: Access to a Chiral Iminophosphorane

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2025-02-27 DOI:10.1021/acs.oprd.4c00532

Felix Xu, Longrui Chen, Dan Lehnherr, François Lévesque

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Abstract

We report the application of rotating cylinder electrode (RCE) reactors for the electrolysis of heterogeneous reactions in batch and in recirculating flow. A scalable method for the synthesis of an N-cyano iminophosphorane ligand in an RCE reactor is also reported. In the development of this process, a graphite felt attached to the inner impervious graphite was used as a rotating anode, and the outer stainless steel wall of the reactor was used as the cathode. The reaction was first evaluated in batch using a small RCE reactor to optimize the spinning rate, supporting electrolyte, and current density. The optimal batch condition was then scaled up in a medium-sized RCE reactor with modifications to adapt it to a flow process. The electrosynthesis was demonstrated up to a 100 g scale, and the impact of the reaction temperature was investigated. Finally, an operationally simple direct crystallization using water as the antisolvent provided a chiral N-cyano iminophosphorane ligand in 74% isolated yield on a 100 g scale from commercially available (S)-BINAP and bis(trimethylsilyl)carbodiimide.

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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.