In Situ Generated Difluoroketene as a C1 Synthon for the [4 + 1] Annulation to 5-Difluoromethyl-1,2,4-oxadiazoles
Abstract Herein, we report an efficient synthesis of 5-difluoromethyl-1,2,4-oxadiazoles through a [4 + 1] annulation process, utilizing in situ generated difluoroketene from readily accessible difluorobromoacetylsilane as the one-carbon building block. This method features simple operation, mild reaction conditions, and broad substrate compatibility with respect to amidoximes. Furthermore, the practicality and robustness of this protocol are further underscored by successful gram-scale reactions and downstream synthetic transformations.
Authors
- Chao Feng (ORCID: https://orcid.org/0000-0003-4494-6845)
- Jie Huang (ORCID: https://orcid.org/0000-0001-8887-2484)
- Jian Zhang (ORCID: https://orcid.org/0000-0001-8734-3003)
- Zhiqiang Li (ORCID: https://orcid.org/0000-0001-6901-4281)
- Xiaolei Zhang (ORCID: https://orcid.org/0000-0001-7267-6737)
- Cheng‐Qiang Wang (ORCID: https://orcid.org/0000-0002-3752-9384)
Institutions
- Nanjing Tech University (CN)
- Hangzhou Normal University (CN)
- Guizhou University (CN)
- Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c03916
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- State Key Laboratory of Materials- Oriented Chemical Engineering