B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>·H<sub>2</sub>O-Catalyzed N–H and C–H Functionalization of Aromatic Amines with Sulfoxonium Ylides under Metal-Free Conditions
Hydrogen-bonded aggregates of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and water are proven as strong Brønsted acid catalysts, which have the advantages of low toxicity and broad compatibility. Sulfoxonium ylides are stable surrogates of diazo compounds, which participate in various reactions due to their versatile reactivity. Based on these characteristics, a strategy for C-N bond or C-C bond construction of aromatic amines with sulfoxonium ylides under metal-free catalytic conditions was established. This method has advantages of mild conditions and excellent yield, which is suitable for the N-H or C-H functionalization of various aromatic amine compounds.
Authors
- Shuran Xu
- Guanghui Lv (ORCID: https://orcid.org/0000-0003-4846-9564)
- Yingdi Hao
- Yong Wu (ORCID: https://orcid.org/0000-0003-0719-4963)
- Li Hai
- Shenmeng Yan
Institutions
- Hubei University of Medicine (CN)
- Sichuan University (CN)
- Taihe Hospital (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-31
- DOI
- https://doi.org/10.1021/acs.joc.4c01558
- Citations
- 3
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.75