Selectfluor‐Mediated Chlorination and Fluorination of Arenes: Late‐Stage Functionalization of APIs and Its Biological Effects

Author:

Gradl Susanne1,Zantop Viviane1,Gmeiner Peter1,Hübner Harald1,Heinrich Markus R.1ORCID

Affiliation:

1. Department of Chemistry and Pharmacy Friedrich-Alexander-Universität Erlangen-Nürnberg Pharmaceutical Chemistry Nikolaus-Fiebiger-Str. 10 91058 Erlangen Germany

Abstract

AbstractBy using active pharmaceutical ingredients (APIs) previously recovered from expired drugs, it is shown that Selectfluor can act as a reagent for operationally simple late‐stage fluorination and chlorination of electron‐rich arenes under mild reaction conditions. As shown in mechanistic experiments, aromatic fluorination thereby competes with chlorine‐for‐fluorine exchange on Selectfluor and subsequent aromatic chlorination, whereat the chloride ions may either be provided by the hydrochloride salt of the respective API or by triethylammonium chloride. Biological testing of the fluorinated or chlorinated APIs at adrenergic, dopaminergic, muscarinergic, opioid or serotoninergic receptors demonstrated that improved binding affinities can be achieved via this straightforward strategy.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

Organic Chemistry,General Pharmacology, Toxicology and Pharmaceutics,Molecular Medicine,Drug Discovery,Biochemistry,Pharmacology

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Recycling: Labor statt Müllcontainer;Nachrichten aus der Chemie;2023-09-29

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