Original Article:
Synthesis of 1,1′-diacetylferrocene imines via catalytic oxo/imido heterometathesis
Andrey V. Pichugov, et al.
Journal of Organometallic Chemistry, 2019, 887, 1-4.
10.1016/j.jorganchem.2019.01.018
It is well known that the chemistry of ferrocene and its derivatives has been extensively developed. 1,1′-Bis(diphenylphosphino)ferrocene-based complexes exhibit high activity in homogeneous catalysis, and their chiral analogues have been successfully used in enantioselective catalysis. Some ferrocene derivatives have been widely concerned because of their anticancer effects. Although ferrocene chemistry is well established and pathways have been developed for direct incorporation of heteroatoms (O, N, P, S, etc.) onto ring carbon atoms or side chain Cα atoms. However, ferrocenyl-based amines are not readily available.
In this work, the authors proposed a novel Cdouble bondN bond forming strategy based on oxo/imido heterometathesis between N-sulfinylamines and ketones, as shown in the figure.
The specific synthesis procedures include:
1. A double-necked Schlenk flask was charged with Ti/SiO2 heterogeneous catalyst, anhydrous toluene, 1,1'-diacetylferrocene, and N-sulfinamide under argon, and the mixture was stirred under reflux.
2. Monitor the reaction by IR spectroscopy, taking aliquots of the reaction mixture until the carbonyl C=O band has completely disappeared at 1676 cm-1.
3. Filter off the catalyst using a glass filter and isolate the product by crystallization from a suitable solvent and dry in vacuo.
Chemicals Related in the Paper:
| Catalog Number | Product Name | Structure | CAS Number | Price |
|---|---|---|---|---|
| ACM1273945 | 1,1'-Diacetylferrocene |  |
1273-94-5 | Price |
