Palladium/tetraphosphine catalyzed suzuki cross-coupling of heteroarylboronic acids with aryl halides (original) (raw)
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Efficient Suzuki cross-coupling reactions using bulky phosphines
Journal of Molecular …, 2006
A series of phosphines, P(biphenyl) n Ph 3−n has been used as co-catalyst in the palladium catalyzed Suzuki cross-coupling reaction of arylbromides and-chlorides. The effects of the phosphine, palladium source, base, solvent and promoter salt were investigated. High conversions and turnovers were obtained in all studied phosphines, particularly using P(biphenyl)Ph 2 which can be interpreted by the contribution of steric and electronic effects.
Suzuki cross-coupling of aryl bromides catalyzed by cyrhetrenylphosphine complexes of palladium (II)
Inorganic Chemistry Communications, 2011
The heterobimetallic Re-Pd complex (CO) 3 Re(η 5 -C 5 H 4 PPh 2 )PdCl 2 (NCMe) I and the chelated complexes (η 5 -C 5 H 4 PPh 2 )(CO) 2 PR 3 Re-PdCl 2 (R = Me, II and R = OMe, III) were used as precatalyst for the Suzuki reaction. Complexes II and III containing a metal-metal bond were shown to be more efficient precatalyst for crosscoupling reaction of a wide range of aryl bromides electronically activated, unactivated and sterically hindered.
A highly efficient catalyst for Suzuki coupling of aryl halides and bromoarylphosphine oxides
Tetrahedron Letters, 2007
The biphenyl-based phosphine, P(o-C 6 H 4 C 6 H 4 Me)Ph 2 , is a moderately bulky and electron-rich phosphine, which has been successfully applied to the palladium catalyzed Suzuki coupling of activated and deactivated aryl halides as well as bromoarylphosphines and bromoarylphosphine oxides, with low catalyst loading and good to excellent conversions and turnovers.
—Palladium–benzimidazolium salt catalyst systems have been studied for the Suzuki coupling. A different substitutent effect has been uncovered with respect to nitrogen substituents in the benzimidazolium salts from the palladium–imidazolium salt analogs. A practical and highly active palladium catalyst system, PdCl 2 /N,N 0-dibenzylbenzimidazolium chloride 2, has been identified for the Suzuki coupling of aromatic halides with arylboronic acids. The coupling of a wide array of aromatic halides with arylboronic acids with the PdCl 2 –2 catalyst system gave good to excellent yields. The effective palladium loading could be as low as 0.0001 mol% and 0.01–0.1 mol% for iodide and bromide substrates, respectively. The coupling of unactivated aromatic chlorides with arylboronic acids also gave good results using Cs 2 CO 3 as base with a 2 mol% palladium loading. The electronic factors from aromatic halides exert a significant influence on the Suzuki coupling catalyzed by the PdCl 2 –2 system while the electronic effect from the arylboronic counterparts is negligible. The aromatic halides with modest steric hindrance could also couple smoothly with phenylboronic acids using the PdCl 2 –2 catalyst system.
Base-Free Suzuki–Miyaura Cross-Coupling Reaction Mediated by Lewis Acids
2021
The palladium-catalyzed Suzuki–Miyaura cross-coupling (SMC) reaction of organohalides and organoborons is a reliable carbon–carbon bond-forming method. This reaction involves a base-mediated transmetalation process, but the presence of a base also promotes competitive protodeborylation, which reduces the efficiency. Herein, we established a base-free SMC reaction via Lewis acid-mediated transmetalation of an organopalladium(II) intermediate with organoborons. Experimental and theoretical investigations indicate that the controlled release of the transmetalation-active intermediate enabled base-free transmetalation under heating conditions and enhanced the applicable scope of this process. This system enabled us to avoid the use of a base, and thus, rendered substrates with base-sensitive moieties available.
Pd-catalyzed Suzuki cross-coupling reactions of glycerol arylboronic esters
Catalysis Communications, 2009
The reaction of glycerol with phenylboronic acid provided a mixture of cyclic glycerol esters, glycerol 1,2phenylboronate (80%), and glycerol 1,3-phenylboronate (20%). The latter two products were formed from the esterification of the 1,2-and 1,3-hydroxyl groups, respectively. The glycerol phenylboronates were applied to the Pd-catalyzed Suzuki cross-coupling reactions with aryl halides, affording the corresponding biphenyl products in high yields. Excess glycerol phenylboronate was not required, and the Suzuki coupling reaction employed a simple catalyst precursor prepared in situ from palladium acetate and triphenylphosphine under mild reaction conditions. Arylboronic acid and pinacol arylboronic ester yielded similar results under the optimized reaction protocol.