Ortho C-H Bond Activations in an Atmospheric Microwave Plasma Ion Source

J Am Soc Mass Spectrom. 2024 May 1;35(5):951-959. doi: 10.1021/jasms.4c00011. Epub 2024 Apr 10.

Abstract

C-H bond ortho-substitution reaction has always been a significant and challenging topic in organic chemistry. We proposed a synthesis method based on microwave plasma torches. High-resolution mass spectrometry was used to monitor rapid reaction products. 2-Alkylbenzimidazole can be formed through the reaction of phenylnitrenium ion and nitriles on a millisecond scale. This reaction can achieve the one-step formation of benzimidazoles from benzene ring single-substituted compounds without the addition of external oxidants or catalysts. A similar C-H bond activation reaction can be accomplished with ketones. Meanwhile, the microwave plasma reactor was modified, and the resulting 2-methylbenzimidazole was successfully collected, indicating the device has good application potential in organic reactions such as C-H bond activation reaction.

Keywords: C−H bond activation; ambient mass spectrometry; gas phase ion chemistry; ion/molecule reactions; plasma chemistry.