Simultaneous Construction of Planar and C–N Axial Chirality Ferrocenes by Pd-Catalyzed Cascade Reaction: Reciprocal Carbonyl-Carbonyl Interaction
A Pd-catalyzed cascade combining asymmetric intramolecular C-H arylation and intermolecular Buchwald-Hartwig coupling constructs ferrocenes with both planar and C-N axial chirality (75% yield, 99% <i>ee</i>, 15:1 <i>d</i>.<i>r</i>.). Kinetic experiments and <i>in situ</i> <sup>31</sup>P NMR confirmed the sequence of the cascade reactions. Moreover, this chirality stems from n-π* interactions and sterics. These ferrocenes are converted diastereoselectively (>20:1 dr) into planar/central chiral phosphine ligands. These ligands enable Pd-catalyzed enantioselective allylic alkylation (85% yield, 97% <i>ee</i>).
Authors
- Wen‐Xiong Zhang (ORCID: https://orcid.org/0000-0003-0744-2832)
- Jianfeng Hu (ORCID: https://orcid.org/0000-0002-1869-6339)
- Yong Yang (ORCID: https://orcid.org/0000-0002-9220-6166)
- Hao Zhang (ORCID: https://orcid.org/0000-0003-2249-3179)
- Yuanyuan Liu
- Junpeng Liu (ORCID: https://orcid.org/0000-0003-2023-4931)
- Congyu Gao
Institutions
- Chinese Academy of Sciences (CN)
- Peking University (CN)
- Inner Mongolia University (CN)
- Institute of Organic Synthesis (RU)
- Beijing National Laboratory for Molecular Sciences (CN)
- Laboratoire de Synthèse Organique (FR)
- Institute of Coal Chemistry (CN)
- Chemical Synthesis Lab (SG)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-23
- DOI
- https://doi.org/10.1021/acs.orglett.5c03568
- Citations
- 2
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.87