23724-92-7Relevant academic research and scientific papers
Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides
Yang, Chu,Zhang, Feng,Deng, Guo-Jun,Gong, Hang
, p. 181 - 190 (2019/01/10)
A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.
Iridium- and rhodium-catalyzed dehydrogenative silylations of C(sp 3) - H bonds adjacent to a nitrogen atom using hydrosilanes
Mita, Tsuyoshi,Michigami, Kenichi,Sato, Yoshihiro
supporting information, p. 2970 - 2973 (2014/01/06)
Now that is just silylated: In the presence of iridium or rhodium catalysts, C(sp3) - H bonds adjacent to a nitrogen atom were silylated by the aid of a pyridine-directing group. In iridium catalysis, a hydrogen-trapping reagent such as norbornene or tert-butylethylene, which is usually required in late transition-metal-catalyzed dehydrogenative coupling reactions, was not required. In rhodium catalysis, however, 1 equivalent of COD (1,5-cyclooctadiene) was necessary to induce higher conversion. Copyright
Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine
Lee, Brian K.,Biscoe, Mark R.,Buchwald, Stephen L.
supporting information; experimental part, p. 3672 - 3674 (2009/10/04)
Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L1Pd(0).
