Chen, Yan-Qiao; Wang, Zhen; Wu, Yongwei; Wisniewski, Steven R.; Qiao, Jennifer X.; Ewing, William R.; Eastgate, Martin D.; Yu, Jin-Quan published their research in Journal of the American Chemical Society on December 26 ,2018. The article was titled 《Overcoming the Limitations of γ- and δ-C-H Arylation of Amines through Ligand Development》.Recommanded Product: 887707-25-7 The article contains the following contents:
L,X-Type transient directing groups (TDGs) based on a reversible imine linkage have emerged as broadly useful tools for C-H activation of ketones and free amines. However, competitive binding interactions among multiple reaction components (TDG itself, substrate, and substrate-TDG adduct) with the palladium catalyst often lead to the formation of multiple unreactive complexes, rendering ligand development extremely challenging. Herein, we report the finding of versatile 2-pyridone ligands that addresses these problems and significantly improves the γ-methylene arylation of alkyl amines, extending the coupling partners to a wide range of medicinally important heteroaryl iodides and even previously unreactive heteroaryl bromides. The combination of an appropriate transient directing group and pyridone ligand has also enabled the δ-arylation of alkyl amines. Notably, our transient directing group design reveals the importance of matching the size of the Pd-chelation with different transient directing groups and the size of palladacycles generated from γ- and δ-C-H bonds: TDGs that coordinate with Pd(II) to form a six-membered chelate are selective toward γ-C-H bonds, whereas TDGs that coordinate with Pd(II) via a five-membered chelate tend to activate δ-C-H bonds. These findings provide an avenue for developing protecting group free and selective C-H functionalization using the transient directing group strategy. In the part of experimental materials, we found many familiar compounds, such as 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Recommanded Product: 887707-25-7)
2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Recommanded Product: 887707-25-7
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com