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Updated: Jul 4, 2025

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DMSO-DCE Triggered Chemodivergent C-Methylenation of Electron-Rich Arenes: An Easy Access to Diarylmethanes
Pallaba Ganjan Dalai1, Swayamprava Swain1, Niranjan Panda1
1Department of Chemistry, National Institute of Technology, Rourkela, Odisha 769008, India.
Abstract:
The chemodivergent property of dimethyl sulfoxide (DMSO) along with 1,2-dichloroethane (DCE) was exploited for the incorporation of a methylene group to form diarylmethanes through a dearomatization/rearomatization process. Methyl(methylene)sulfonium ions (CH2=S+-Me) were generated by simple heating of commonly used solvents such as DMSO and DCE. These ions were subsequently trapped by electron-rich arenes and heteroarenes, resulting in the synthesis of both symmetrical and unsymmetrical diarylmethanes. This protocol was further extended to access N-methylenamides by reacting 2-naphthol with amides or nitriles in the presence of DMSO and DCE.
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