170891-76-6Relevant academic research and scientific papers
Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary
Wei, Yu,Tang, Huarong,Cong, Xuefeng,Rao, Bin,Wu, Chao,Zeng, Xiaoming
supporting information, p. 2248 - 2251 (2014/05/06)
An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.
Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp 2 and sp3 carbon-hydrogen bonds
Shabashov, Dmitry,Daugulis, Olafs
supporting information; experimental part, p. 3965 - 3972 (2010/05/15)
We have developed a method for auxiliary-directed, palladium-catalyzed β-arylation and alkylation of sp3 and sp2 C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp3 C-H bonds can be achieved. If arylation of secondary sp 3 C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp3 and sp2 C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.
