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Improved palladium-catalyzed coupling reactions of aryl halides using saturated N-heterocarbene ligands
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In this paper, saturated N -heterocyclic carbenes were incorporated into palladium pre-catalysts to give high catalyst activity in the Suzuki coupling of aryl iodides, bromides and deactivated aryls chloride substrates.Abstract:
The incorporation of saturated N -heterocyclic carbenes into palladium pre-catalysts gives high catalyst activity in the Suzuki coupling of aryl iodides, bromides and deactivated aryl chloride substrates, whereas the yield of the palladium catalyzed Heck reaction of deactivated aryl chlorides is negligible. The complexes were generated in the presence of Pd(OAc) 2 by in situ deprotonation of 1,3-dialkylimidazolinium salts LHX ( 1 ) which were characterized by conventional spectroscopic methods and elemental analyses.read more
Citations
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Selective palladium-catalyzed arylation(s) of benzaldehyde derivatives by N-heterocarbene ligands
TL;DR: In this article, the 2- or 2-6-position of aromatic aldehydes were directly and selectively arylated with aryl chlorides or bromides in the presence of a catalytic system.
Journal ArticleDOI
Ferrocenyl monophosphine ligands: synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides.
TL;DR: The electron-rich phosphines have been successfully applied to the Suzuki-Miyaura coupling of activated and deactivated aryl chlorides, with low catalyst loading being feasible in the synthesis of tris-ortho-substituted biaryls.
Journal ArticleDOI
Ruthenium(II) N -heterocyclic Carbene Complexes in the Transfer Hydrogenation of Ketones
TL;DR: In this paper, the reduction of ketones to alcohols via transfer hydrogenation was achieved with catalytic amounts of ruthenium-N-heterocyclic carbene complexes (2−7) in the presence of t-BuOK.
Journal ArticleDOI
Palladium–benzimidazolium salt catalyst systems for Suzuki coupling: development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids
TL;DR: In this article, a practical and highly active palladium catalyst system, PdCl 2 / N, N ′-dibenzylbenzimidazolium chloride 2, has been identified for the Suzuki coupling of aromatic halides with arylboronic acids.
Journal ArticleDOI
Synthesis, characterization and the Suzuki-Miyaura coupling reactions of N-heterocyclic carbene-Pd(II)-pyridine (PEPPSI) complexes
TL;DR: In this article, a new series of air and moisture-stable NHC-PdCl 2 -pyridine complexes, (2a-f ) have been described with the development of a more efficient catalytic system for the cross-coupling of aryl halides in mind.
References
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Journal ArticleDOI
Palladium-catalyzed cross-coupling reactions of organoboron compounds
Norio Miyaura,Akira Suzuki +1 more
TL;DR: In this paper, a cross-coupling reaction is proposed for coupling 1 -Alkenylboron Derivatives: Synthesis of Conjugated Dienes 6.
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Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.
TL;DR: These air- and water-tolerant complexes were shown to exhibit an increased ring-closing metathesis activity at elevated temperature when compared to that of the parent complex 2 and the previously developed complex 3.
Journal ArticleDOI
Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998
TL;DR: The palladium-catalyzed cross-coupling reaction between organoboron compounds and organic halides or triflates provides a powerful and general methodology for the formation of carbon-carbon bonds as discussed by the authors.
Journal ArticleDOI
Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
Adam F. Littke,Gregory C. Fu +1 more
TL;DR: This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.
Journal ArticleDOI
Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions
TL;DR: In this paper, the authors used Pd2(dba)3/P(t-Bu)3 as a catalyst for Suzuki cross-coupling of aryl and vinyl triflates.
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Palladium-catalyzed cross-coupling reactions of organoboron compounds
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