Access to 4-methylene-phospholenes through BF<sub>3</sub>·Et<sub>2</sub>O catalyzed isomerization of 3,4-dimethylphosphole sulfides
We have developed a practical synthetic approach to 4-methylene-phospholene derivatives through BF<sub>3</sub>·Et<sub>2</sub>O-catalyzed isomerization of 3,4-dimethylphosphole sulfides. The reaction simultaneously establishes a P-stereocenter while performing skeletal rearrangement. The transformation is enabled by the weak antiaromatic character of the phosphole sulfides, which facilitates the thermodynamically favoured migration of an endocyclic double bond to the exocyclic terminal position.
Authors
- Lihui Chen (ORCID: https://orcid.org/0000-0001-8864-5660)
- Rongqiang Tian (ORCID: https://orcid.org/0000-0002-5460-1691)
- Yingqiang Wang
- Meng Xiao (ORCID: https://orcid.org/0000-0003-2103-7008)
Institutions
- Zhengzhou University (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00940e
- Primary Topic
- Organophosphorus compounds synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00