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FluoroFusion: NHC-Catalyzed Nucleophilic Aromatic Substitution Reaction Unveils Functional Perfluorinated Diarylmethanones.

ABSTRACT: A mild, facile, and metal-free approach via the N-heterocyclic carbene-catalyzed S_NAr reaction between aryl aldehydes with perfluoroarenes to obtain the coveted functional perfluorinated diarylmethanones is disclosed. This method accommodates a diverse substrate range and exhibits notable tolerance toward various functional groups. Our success in modifying biologically relevant molecules, crafting a fully fluorinated bioisosteric analogue of drug candidate D1, and highlighting the potential of these ketones as valuable electrolyte additives for lithium-ion batteries (LIBs) underscores the versatility of our methodology.

SUBMITTER: Chan CL

PROVIDER: S-EPMC10964231 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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FluoroFusion: NHC-Catalyzed Nucleophilic Aromatic Substitution Reaction Unveils Functional Perfluorinated Diarylmethanones.

Chan Cheng-Lin CL Lee Shao-Chi SC Lin Pei-Shan PS Tapales Radyn Vanessa Phaz P RVPP Li Jia-Syuan JS Lai Chun-An CA Lee Jyh-Tsung JT Li Chien-Hung CH Liao Hsuan-Hung HH

Organic letters 20240308 11

A mild, facile, and metal-free approach via the N-heterocyclic carbene-catalyzed SNAr reaction between aryl aldehydes with perfluoroarenes to obtain the coveted functional perfluorinated diarylmethanones is disclosed. This method accommodates a diverse substrate range and exhibits notable tolerance toward various functional groups. Our success in modifying biologically relevant molecules, crafting a fully fluorinated bioisosteric analogue of drug candidate D1, and highli ...[more]

PMID: 38458971

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