Author
Isabelle Kondolff
Other affiliations: Aix-Marseille University
Bio: Isabelle Kondolff is an academic researcher from Université Paul Cézanne Aix-Marseille III. The author has contributed to research in topics: Aryl & Coupling reaction. The author has an hindex of 5, co-authored 10 publications receiving 144 citations. Previous affiliations of Isabelle Kondolff include Aix-Marseille University.
Topics: Aryl, Coupling reaction, Palladium, Suzuki reaction, Catalysis
Papers
More filters
TL;DR: The synthesis of biheteroaryl derivatives by palladium-catalysed Suzuki cross-coupling reaction of heteroaryl bromides with hetero-boronic acids is a challenging reaction due to the electronic and/or poisoning properties of these heter-oaryl compounds as mentioned in this paper.
Abstract: The synthesis of biheteroaryl derivatives by palladium-catalysed Suzuki cross-coupling reaction of heteroaryl bromides with heteroarylboronic acids is a challenging reaction due to the electronic and/or poisoning properties of these heteroaryl compounds. Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of heteroaryl bromides undergoes Suzuki reaction with heteroarylboronic acids such as thiophene-, furan- or pyridineboronic acid derivatives in good yields. This catalyst can be used at low loadings with several substrates. In general bromopyridines were found to be more reactive than bromothiophenes or bromofuranes.
39 citations
TL;DR: The Suzuki and Heck reactions of aryl di-, tri-, or tetrabromides with a range of acids or alkenes with moderate to high ratio substrate/catalyst in good yields have been successfully used.
38 citations
TL;DR: A tetraphosphine, all- cis -3-(2-diphenylphosphinoethyl)-1,2,4-tris(diphosphinomethyl)cyclopentane (Ditricyp) was synthesized in seven steps from commercially available dicyclopentadiene as discussed by the authors.
28 citations
TL;DR: In this paper, the Suzuki reaction of hetero-boronic acids with aryl bromides and also the coupling of arylsboronic acid with heteroaryl bromide was studied.
23 citations
TL;DR: In this article, a range of aryl bromides undergo Heck reaction with ethylene glycol vinyl ether, in the presence of [PdCl(C3H5)]2/cis,ciscis-1,2,3,4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as catalyst, to give regioselectively protected β-arylation products in good yields.
20 citations
Cited by
More filters
TL;DR: The emergence of organotrifluoroborates has provided important new perspectives for the organoboron component of these reactions, and in combination, these two components prove to be extraordinarily powerful partners for cross-coupling reactions.
Abstract: Monocoordinated palladium catalysts derived from sterically hindered, electron-rich phosphines or N-heterocyclic carbenes have revolutionized the Suzuki–Miyaura coupling reaction. The emergence of organotrifluoroborates has provided important new perspectives for the organoboron component of these reactions. In combination, these two components prove to be extraordinarily powerful partners for cross-coupling reactions.
376 citations
TL;DR: The general purpose of this review is to give an exhaustive and clear picture in heteroaryl-heteroaryl bond formation as well as its application in the synthesis of natural products, pharmaceuticals, catalyst ligands, and materials.
Abstract: The biheteroaryl structural motif is prevalent in polymers, advanced materials, liquid crystals, ligands, molecules of medicinal interest, and natural products. Many types of synthetic transformations have been known for the construction of heteroaryl–heteroaryl linkages. Coupling reactions provide one of the most efficient ways to achieve these biheterocyclic structures. In this review, four types of coupling reactions are discussed: 1) transition-metal-catalyzed coupling reactions of heteroaryl halides or surrogates with heteroarylmetals; 2) direct inter- and intramolecular heteroarylations of CH bonds of heteroarenes with heteroaryl halides or pseudohalides; 3) oxidative CH/CH homo- and cross-couplings of two unpreactivated heteroarenes; and 4) transition-metal-catalyzed decarboxylative cross-coupling reactions between haloheteroarenes or heteroarenes and heteroarenecarboxylic acids. The general purpose of this review is to give an exhaustive and clear picture in heteroaryl–heteroaryl bond formation as well as its application in the synthesis of natural products, pharmaceuticals, catalyst ligands, and materials.
272 citations
TL;DR: The present cross-coupling reaction catalyzed by iron-group metal fluorides and an NHC ligand provides a highly selective and practical method for the synthesis of unsymmetrical biaryls as well as the opportunity to gain new mechanistic insights into the metal-catalyzed cross-Coupling reactions.
Abstract: Combinations of N-heterocyclic carbenes (NHCs) and fluoride salts of the iron-group metals (Fe, Co, and Ni) have been shown to be excellent catalysts for the cross-coupling reactions of aryl Grignard reagents (Ar1MgBr) with aryl and heteroaryl halides (Ar2X) to give unsymmetrical biaryls (Ar1−Ar2). Iron fluorides in combination with SIPr, a saturated NHC ligand, catalyze the biaryl cross-coupling between various aryl chlorides and aryl Grignard reagents in high yield and high selectivity. On the other hand, cobalt and nickel fluorides in combination with IPr, an unsaturated NHC ligand, exhibit interesting complementary reactivity in the coupling of aryl bromides or iodides; in contrast, with these substrates the iron catalysts show a lower selectivity. The formation of homocoupling byproducts is suppressed markedly to less than 5% in most cases by choosing the appropriate metal fluoride/NHC combination. The present catalyst combinations offer several synthetic advantages over existing methods: practical s...
265 citations
TL;DR: This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures and obtained in good to excellent yields.
Abstract: A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.
217 citations
213 citations