Synthesis of biphenyl-based arsine ligands by Suzuki–Miyaura coupling and their application to Pd-catalyzed arsination

Abstract

A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh(2) moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu(3)SnAsPh(2) (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (R(f)I). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%).

PVP-stabilized palladium nanoparticles electrochemically obtained as effective catalysts in aqueous medium Suzuki–Miyaura reaction

“…For this study, based on previous results [68] and after a series of initial experiments, H 2 O:EtOH 75:25 was chosen as the solvent and K 3 PO 4 as the base. The reactions were performed at 90 • C under nitrogen atmosphere in the presence of different ratios of PdNPs as catalyst within 24 h. Under this reaction condition we evaluated all the NPs electrochemically synthesized without any purification.…”

Synthesis, Characterization, and Nanocatalysis Application of Core–Shell Superparamagnetic Nanoparticles of Fe3O4@Pd

“…Based on our previous results, [48,49] and after a series of initial experiments, the reactions were performed with K 3 PO 4 as the base and in the presence of 1.5 mol % of Pd, employing SPNPs Fe 3 O 4 @Pd-OA as catalyst under a nitrogen atmosphere (Fig. 10).…”

Computational Study on the C–Heteroatom Bond Formation via Stille Cross-Coupling Reaction: Differences between Organoheterostannanes Me3SnAsPh2vs Me3SnPPh2

“…7c,8 In addition, this procedure has been helpful toward the synthesis of functionalized triarylarsines and arsine ligands. 8b, 9 Both the Pd-catalyzed arsination and phosphination reactions could be carried out using a wide variety of aryl iodides, including those sterically hindered, in the presence of different functional groups and achieving high yields of the corresponding coupling product. 7a,c,d,8 However, it was not possible to successfully accomplish similar transformations involving aryl bromides and chlorides under many tested reaction conditions, including those in which these halides have proven to produce new C−C bonds.…”