Alkali-Metal-Catalyzed Deprotonative Addition of Toluenes with Styrenes
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Updated: Sep 19, 2025
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Yuanyun Gu1, Yufei Zhang1, Yaqi Yuan1
1State Key Laboratory of Materials Oriented Chemical Engineering (MCE), Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.
Abstract:
A LiN(SiMe3)2/CsF-catalyzed benzylic C-H bond addition of toluene to styrene is reported, which enables the functionalization of weakly acidic C-H bonds (pKa ≈ 43) with high efficiency and a broad substrate scope. This method overcomes the limitations of traditional strong base systems by utilizing a bimetallic catalyst that reversibly deprotonates benzylic positions, achieving yields of 62-89% across 34 examples. Key advantages include excellent functional group tolerance, scalability, and operational simplicity. Mechanistic studies, supported by kinetic isotope effects, confirm that benzylic deprotonation is the turnover-limiting step.
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