A General Method for the Suzuki−Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides:  Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature

Abstract

The catalytic formation of di- and trisubstituted ortho biaryl junctions has been achieved using a palladacylce pre-catalyst bearing a N-heterocyclic carbene ligand. This transformation is performed at room temperature in technical grade 2-propanol.

Polymer precursors from catalytic reactions of natural oils

“…The Suzuki-Miyaura coupling under mild conditions was successfully performed by Nolan and co-workers using isopropanol as a solvent. 263 The same group later developed a methodology for the reduction/trapping of Pd(II) complexes into the carbene-phosphine mixed Pd(0) species in isopropanol, the latter playing the role of a reducing agent via the isopropoxide anion. 259 Considering the advantages of isopropanol, it was therefore chosen as an additive.…”

Crystal structure of [2-(4-methoxyphenyl)pyrazine-κ2 C,N) chlorido[N,N′-bis-(2,6-diisopropyl-phenyl)imidazol-2-ylidene-κC)] palladium(II), C38H45ClN4OPd

“…A number of reports have shown that phosphines adducts of palladacycles are a ective catalysts for this transformation [4,5]. As an alternative, the N-heterocyclic carbenes (NHCs) adducts of palladacycles have been proved to be excellent precatalysts [6,7]. Moreover, the use of NHCs as ancillary ligands has opened up new routes for the design of emitting materials, because of their excellent color purity and high stability [8,9].…”

Formation and growth of palladium nanoparticles inside porous poly(4-vinyl-pyridine) monitored by operando techniques: The role of different reducing agents

“…As discussed in the introduction, alcohols are often used as solvents in reactions catalyzed by Pdbased catalysts [33], or they may be used even as reactants [34][35][36][37][38][39][40][41]. Therefore, it is important to clarify if they are innocent toward the catalyst, or if they may react with it and eventually lead to its final deactivation.…”

“…Indeed, palladium-catalyzed reactions (e.g. hydrogenation, Suzuki-Miyaura Cross-Coupling reaction, and others) [33] are often conducted in slurry conditions, using alcohols as solvents, because alcohols combine good solvation properties for organic compounds with a low price. Hence, understanding the role of alcohols in palladium-catalyzed reactions is of prime interest in the optimization of the reaction variables.…”