P,N Hemilabile Ligand-Enabled Palladium-Catalyzed Dearomative Allylation of α-(Trialkylsilyl) Benzyl Chlorides
The first dearomative allylation of <i>a</i>-(trialkylsilyl) benzyl chlorides with allyltributylstannane via R<sub>3</sub>Si-Pd-π-benzyl intermediates is described. The reactions proceeded smoothly in the presence of a specific P,N hemilabile ligand to generate vinylsilanes bearing an allyl group in satisfactory to good yields. Systematic evaluation of phosphine ligands identified ESPmin and % Vbur (min) as key parameters correlating ligand structure with catalytic activity. Computational investigations supported experimental findings, offering mechanistic insights into the dearomative allylation.
Authors
- Ming Bao (ORCID: https://orcid.org/0000-0002-5179-3499)
- Yuxin Yao (ORCID: https://orcid.org/0000-0002-9358-7730)
- Zhangrong Lou (ORCID: https://orcid.org/0009-0006-9352-6002)
- Sheng Zhang (ORCID: https://orcid.org/0000-0002-9671-7668)
- Yilin Zhao (ORCID: https://orcid.org/0000-0003-1486-9500)
- Ya Gao
Institutions
- Dalian University of Technology (CN)
- Dalian University (CN)
- Smart Material (Germany) (DE)
- State Key Laboratory of Fine Chemicals
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-09
- DOI
- https://doi.org/10.1021/acs.joc.5c01046
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00