期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 44, 页码 23557-23563出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202108465
关键词
aliphatic acid; copper; photocatalysis; polyfluoroarylation; reaction mechanisms
资金
- Swiss National Science Foundation [200021_181977]
- NCCR Catalysis, a National Centre of Competence in Research - Swiss National Science Foundation
- Ecole Polytechnique Federale de Lausanne
- Swiss National Science Foundation (SNF) [200021_181977] Funding Source: Swiss National Science Foundation (SNF)
The study presents a decarboxylative coupling reaction using photoredox and copper catalysis to convert alkyl carboxylic acids into polyfluoroaryl compounds. The method demonstrates broad scope and good functional group compatibility, with the potential to achieve a wide range of F-substitution patterns on the aryl groups. Mechanistic study suggests a [Cu-(Ar-F)(2)] species may be responsible for the transfer of polyfluoroaryl groups to alkyl radicals.
Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carboxylic acids with polyfluoroaryl zinc reagents (Zn-Ar-F) via synergetic photoredox and copper catalysis. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding polyfluoroaryl compounds, which could have a wide range of F-content (2F-5F) and variable F-substitution patterns on the aryl groups. Broad scope and good functional group compatibility were achieved, including on substrates derived from natural products and pharmaceuticals. Mechanistic study revealed that a [Cu-(Ar-F)(2)] species could be responsible for the transfer of polyfluoroaryl groups to the alkyl radicals.
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