Ligand-Controlled Preparation of Aryl-Substituted Allenes Enabled by Nickel-Catalyzed Reductive Coupling of Secondary Propargylic Carbonates with Aryl Halides
Herein, we developed a new method for the synthesis of aryl-substituted allenes through a nickel-catalyzed reductive coupling reaction between secondary propargyl carbonates and aryl halides. By employing the dimethyl-1,10-phenanthroline ligand, we achieved a ligand-controlled, regioselective nickel-catalyzed reductive arylation, overcoming the structural limitations of propargyl electrophiles. Notably, this reaction exhibits exceptional functional group compatibility, rendering it particularly suitable for late-stage allenylation modifications of complex molecules.
Authors
- Hegui Gong (ORCID: https://orcid.org/0000-0001-6534-5569)
- Wenhai Huang (ORCID: https://orcid.org/0000-0003-1457-7380)
- Jie Hu (ORCID: https://orcid.org/0000-0002-7598-5153)
- Ruotong Li (ORCID: https://orcid.org/0000-0002-0882-8510)
- Yonghao Xi
Institutions
- Shanghai University (CN)
- Henan University (CN)
- Center for NanoScience (DE)
- College of Medical Sciences (NP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-15
- DOI
- https://doi.org/10.1021/acs.orglett.5c01235
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Natural Science Foundation of Shanghai
- National Natural Science Foundation of China