A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

Abstract

The Suzuki-Miyaura reaction of various aryl halides with aryl boronic acids using {[Ph 2 PCH 2 PPh 2-CH=C(O)(C 10 H 7 )]PdCl 2 } as a catalyst has been investigated. The X-ray crystal structure of the catalyst reveals a five-membered chelate ring formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal center. This palladacycle exhibited excellent activities and reusability in the aqueous phase for the Suzuki cross-coupling reactions of arylboronic acids with aryl halides. The proposed protocol featured mild reaction conditions and notable simplicity and efficiency using Cs 2 CO 3 as a base in water. The catalytic system could be reused four times without significant loss of activity.

Spectral, crystallographic, theoretical and antibacterial studies of palladium(II)/platinum(II) complexes with unsymmetric diphosphine ylides

“…The dihedral angle between the keto group and the cyano‐substituted aromatic ring is 16.1(2)°. The structure is similar to that of other Pd ylide complexes, such as dichloro‐(1‐(((diphenylphosphino)methyl)(diphenyl)phosphonio)‐2‐(2‐naphthyl)‐2‐oxoethyl)palladium(II) and (2‐(biphenyl‐4‐yl)‐1‐(((diphenylphosphino)methyl)(diphenyl)phosphonio)‐2‐oxoethyl)(dichloro)palladium …”

Recent Advances in the Palladium Catalyzed Suzuki–Miyaura Cross-Coupling Reaction in Water

“…[22] In a very recent study, Khazalpour and co-workers reported the palladium-phosphine system 7 as an active and recyclable pre-catalyst for SMC in water. [23] A fivemembered chelate ring is formed upon coordination of the ligand through the phosphine and the ylidic carbon atom. The catalytic system could be reused four times without significant loss of activity (Scheme 7).…”

Pallada‐ and platinacycle complexes of phosphorus ylides; synthesis, X‐ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki‐Miyaura coupling reaction

“…Pt(I) and Pt(III) complexes are noted for instability and any reduction or oxidation processes centralized on metal orbitals of Pt(II) complexes typically exhibit irreversible behavior . In 4 , such as 3 , peak C 4 (− 0.77 V) is assigned to the two electron reduction of Pd(II) center in the complex and the second reduction peak, C Y2 (− 0.49 V), is related to the reduction of ylide Y 2 (Figure , curve d) . The overall two‐electron reduction of the Pd(II) complexes is expected to take place in separate one‐electron steps and this might be achieved via manipulation of the thermodynamics or electrode kinetics of either step by correct choice of the experimental conditions.…”