DMSO–DCE Triggered Chemodivergent C-Methylenation of Electron-Rich Arenes: An Easy Access to Diarylmethanes
Pallaba Ganjan Dalai, Swayamprava Swain, Niranjan Panda
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 (CH 2 =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.
Topics & Concepts
SulfoniumChemistryMethyleneIonDimethyl sulfoxideMedicinal chemistryOrganic chemistrySalt (chemistry)Catalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis