Palladium-catalyzed Suzuki (palladium-catalyzed + suzuki)

Distribution by Scientific Domains


Selected Abstracts


Palladium-Catalyzed Suzuki,Miyaura Cross-Coupling Using Phosphinous Acids and Dialkyl(chloro)phosphane Ligands

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 8 2006
Christian Wolf
Abstract The use of eleven palladium complexes having monomeric and ,-chloro-bridged dimeric structures and either bulky dialkyl- and diarylphosphinous acid ligands (POPd, POPd-Br, POPd1, POPd2, POPd6, POPd7, Ph1-Phoxide) or dialkyl(chloro)phosphane ligands (PXPd, PXPd2, PXPd6, PXPd7) for Suzuki,Miyaura coupling reactions has been evaluated. Screening and optimization of catalyst loading, solvent, temperature, and base showed that excellent results can be obtained with electron-deficient and electron-rich aryl iodides, bromides, and chlorides in the presence of 2.5 mol-% of palladium,phosphinous acid POPd, (tBu2POH)2PdCl2, in 1,4-dioxane using cesium carbonate as base. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]


Palladium-Catalyzed Suzuki,Miyaura Reactions of Potassium Aryl- and Heteroaryltrifluoroborates with Aryl- and Heteroaryl Triflates.

CHEMINFORM, Issue 48 2005
Gary A. Molander
Abstract For Abstract see ChemInform Abstract in Full Text. [source]


2,3-Disubstituted Benzo[b]thiophenes from Diarylalkynes via Electrophilic Addition-Cyclization and Palladium-Catalyzed Cross-Coupling

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 13 2007
Giuseppe Lamanna
Abstract Diarylalkynes are readily transformed in 3-chlorobenzo[b]thiophenes in a two-step electrophilic addition-cyclization procedure that runs highly efficiently in solution or in the solid phase. The heteroaromatic carbon-chlorine bond participates in palladium-catalyzed Suzuki,Miyaura or Buchwald,Hartwig cross-couplings to give, in a single step, 2,3-disubstituted derivatives of pharmacological relevance . [source]


2-Pyridylquinoxaline derivatives as N,N -ligands for palladium-catalyzed Suzuki,Miyaura reaction

APPLIED ORGANOMETALLIC CHEMISTRY, Issue 8 2009
Yundong Liu
Abstract The Suzuki,Miyaura reaction of aryl bromides with benzeneboronic acid catalyzed by bis(chloro)(2-pyridylquinoxaline)palladium(II) was investigated. The scope of the bis(chloro)(2-pyridylquinoxaline)palladium(II) was determined in toluene at 80 °C using KOH as base. Using a 0.1% molar ratio of bis(chloro)(2-pyridylquinoxaline)palladium(II) C1 as a catalyst, aryl bromides reacted with benzeneboronic acid to afford diaryl derivatives in excellent yield. Copyright © 2009 John Wiley & Sons, Ltd. [source]


Enantioselective Synthesis of Non-Natural Aromatic ,-Amino Acids

CHEMISTRY - A EUROPEAN JOURNAL, Issue 2 2004
Andreas Krebs
Abstract We present two complementary methods for the stereoselective synthesis of non-natural ,-amino acids with aromatic or heteroaromatic side chains. One approach is based on the chemical transformation of methionine, whereas the other applies the stereoselective Myers alkylation of glycine. The resulting product types differ in the linker length between glycine and the aromatic substituent. Since methionine and pseudoephedrine are available in both absolute configurations, R - or S -configured enantiopure amino acids with either C2 or C3 linkers can be obtained on gram scales. In each case the key step of the synthesis is hydroboration of the unsaturated building blocks 9 and 17, followed by palladium-catalyzed Suzuki cross-coupling with aryl halides. Attention must in certain cases be paid to the stereochemical integrity when basic Suzuki conditions are applied. Our initial difficulties are reported as well as the final "racemization-proof" procedures. The protecting groups chosen for the ,-amino acids should be compatible with solid-phase peptide synthesis. This was confirmed by the successful synthesis of a series of tripeptides. [source]