Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates
Herein, we report a general and efficient Ni-catalyzed reductive cross-coupling reaction of substituted vinyl bromides and α-chloro phosphonates to access a set of α-vinyl phosphonates using zinc as the terminal reductant. This reaction exhibits broad substrate adaptability and good functional group tolerance, which allows to afford diverse compounds including structurally complex motifs from natural products and drugs. Furthermore, the practicality was certificated through the gram-scale and transformation experiments. The preliminary mechanistic investigations support a radical chain process. The potential to realize enantiomeric control makes it more valuable for further exploration.
Authors
- Tian Xie (ORCID: https://orcid.org/0000-0001-7066-1443)
- Yang Ye (ORCID: https://orcid.org/0000-0001-5279-8104)
- Liwei Wang (ORCID: https://orcid.org/0000-0003-4990-9445)
- Huimin Yang (ORCID: https://orcid.org/0000-0002-4432-6868)
- Liang Zou (ORCID: https://orcid.org/0009-0002-2591-5584)
Institutions
- Hangzhou Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-18
- DOI
- https://doi.org/10.1021/acs.joc.4c01929
- Citations
- 2
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.42
Funders
- National Natural Science Foundation of China
- Hangzhou Normal University
- Department of Education of Zhejiang Province
- Medical Science and Technology Project of Zhejiang Province