Alkali-Metal-Catalyzed Deprotonative Addition of Toluenes with Styrenes
A LiN(SiMe<sub>3</sub>)<sub>2</sub>/CsF-catalyzed benzylic C-H bond addition of toluene to styrene is reported, which enables the functionalization of weakly acidic C-H bonds (p<i>K</i><sub>a</sub> ≈ 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.
Authors
- Yan‐En Wang (ORCID: https://orcid.org/0000-0001-7039-0495)
- Jianyou Mao (ORCID: https://orcid.org/0000-0003-0581-3978)
- Yuanyun Gu (ORCID: https://orcid.org/0000-0002-7868-0822)
- Yaqi Yuan (ORCID: https://orcid.org/0009-0001-4740-6468)
- Dan Xiong (ORCID: https://orcid.org/0000-0003-0722-8668)
- Yufei Zhang (ORCID: https://orcid.org/0000-0002-5890-3056)
Institutions
- Hebei Agricultural University (CN)
- Nanjing Tech University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-06
- DOI
- https://doi.org/10.1021/acs.orglett.5c01842
- Citations
- 1
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.54
Funders
- State Key Laboratory of Materials- Oriented Chemical Engineering
- Jiangsu Provincial Key Research and Development Program