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

Abstract

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.

Graphical Abstract

Keywords:

• 2-Nitromethyl aromatic ketone
• α-nitroketone
• benzyne
• inserion

Additional information

Funding

The authors thank the financial support by Education Department of Sichuan Provincial [No. 14ZA0349].