Facile synthesis of 2-nitromethyl aromatic ketones by insertion of benzynes into the C-C bond of α-nitroketones

A facile method to synthesize 2-nitromethyl aromatic ketones was developed. In the method, benzyne was generated in situ for the insertion to α-Nitroketones in one pot to achieve 2-nitromethyl aromatic ketones under mild conditions. Aromatic and aliphatic α-nitroketones were applied in the reaction,...

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Bibliographic Details
Published inSynthetic communications Vol. 49; no. 4; pp. 558 - 562
Main Authors Hu, Ji-Hong, Zheng, Hong-Jie
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 16.02.2019
Taylor & Francis Ltd
Subjects
2-Nitromethyl aromatic ketone
Aliphatic compounds
benzyne
Chemistry
Chemistry, Organic
inserion
Insertion
Ketones
Physical Sciences
Science & Technology
Substrates
Synthesis
α-nitroketone
PALLADIUM
benzyne
CHEMOSELECTIVE HYDROGENATION
inserion
alpha-nitroketone
ARYNES
2-Nitromethyl aromatic ketone
STRAIGHTFORWARD SYNTHESIS
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Summary:A facile method to synthesize 2-nitromethyl aromatic ketones was developed. In the method, benzyne was generated in situ for the insertion to α-Nitroketones in one pot to achieve 2-nitromethyl aromatic ketones under mild conditions. Aromatic and aliphatic α-nitroketones were applied in the reaction, and the results show that aliphatic α-nitroketones gave excellent yields (up to 96%), while aromatic α-nitroketones gave moderate yields. The synthesized 2-nitromethyl aromatic ketones could be potential substrates to synthesize isoindoles.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2018.1563794