Demethylation C–C coupling reaction facilitated by the repulsive Coulomb force between two cations

Xiaoping Zhang, Keke Huang, Yanlin Fu, Ni Zhang, Xianglei Kong, Yuanyuan Cheng, Mingyu Zheng, Yihao Cheng, Tenggao Zhu, Bina Fu (), Shouhua Feng () and Huanwen Chen ()
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Xiaoping Zhang: East China University of Technology
Keke Huang: Jilin University
Yanlin Fu: Chinese Academy of Sciences
Ni Zhang: Jiangxi University of Chinese Medicine
Xianglei Kong: Nankai University
Yuanyuan Cheng: East China University of Technology
Mingyu Zheng: East China University of Technology
Yihao Cheng: East China University of Technology
Tenggao Zhu: Jiangxi University of Chinese Medicine
Bina Fu: Chinese Academy of Sciences
Shouhua Feng: Jilin University
Huanwen Chen: East China University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Carbon chain elongation (CCE) is normally carried out using either chemical catalysts or bioenzymes. Herein we demonstrate a catalyst-free approach to promote demethylation C–C coupling reactions for advanced CCE constructed with functional groups under ambient conditions. Accelerated by the electric field, two organic cations containing a methyl group (e.g., ketones, acids, and aldehydes) approach each other with such proximity that the energy of the repulsive Coulomb interaction between these two cations exceeds the bond energy of the methyl group. This results in the elimination of a methyl cation and the coupling of the residual carbonyl carbon groups. As confirmed by high-resolution mass spectrometry and isotope-labeling experiments, the C–C coupling reactions (yields up to 76.5%) were commonly observed in the gas phase or liquid phase, for which the mechanism was further studied using molecular dynamics simulations and stationary-point calculations, revealing deep insights and perspectives of chemistry.

Date: 2024
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DOI: 10.1038/s41467-024-49946-y

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