Author
Jean-Francis Spindler
Other affiliations: Centre national de la recherche scientifique, Rhône-Poulenc, École nationale supérieure de chimie de Montpellier
Bio: Jean-Francis Spindler is an academic researcher from Rhodia. The author has contributed to research in topics: Aryl & Catalysis. The author has an hindex of 10, co-authored 31 publications receiving 1601 citations. Previous affiliations of Jean-Francis Spindler include Centre national de la recherche scientifique & Rhône-Poulenc.
Topics: Aryl, Catalysis, Nitrile, Raney nickel, Leaving group
Papers
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TL;DR: The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles, providing the arylated products under particularly mild conditions.
Abstract: Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions (50-82 degrees C). The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al (1c) generates a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of diethyl malonate, ethyl cyanoacetate, and malononitrile with aryl iodides under mild conditions (50-82 degrees C). The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles.
542 citations
TL;DR: Copper-catalysed Narylation of pyrazoles with aryl or heteroaryl bromides or iodides, which can include functional substituents, was performed under the mildest conditions yet described, by the use as catalyst of a combination of cuprous oxide with a set of inexpensive, chelating oxime-type ligands not previously known to promote such reactions.
275 citations
TL;DR: An efficient method for the synthesis of diaryl ethers under particularly mild conditions is described, and inexpensive ligands were found to greatly accelerate the Ullmann-type coupling of aryl bromides or iodides with phenols.
272 citations
TL;DR: In this article, the cross-coupling of aliphatic and aromatic thiols and aryl bromides/triflates mediated by a Pd2(dba)3/Xantphos catalytic system in refluxing xylene (140°C) affords the corresponding thioethers in good yield.
154 citations
TL;DR: In this paper, the Ullmann-type synthesis of diaryl ethers was shown to operate at 60-80 °C, the lowest temperatures reported to date for an Ullman type synthesis.
Abstract: Coupling of phenols and aryl bromides can be efficiently performed by means of catalytic amounts of copper iodide and the inexpensive ligand 1 (structure given in Table 1). The reaction is applicable to a wide range of substrates and proceeds at 60-80 °C, the lowest temperatures reported to date for an Ullmann-type synthesis of diaryl ethers. Moreover, the use of aryl bromides and inexpensive K 3 PO 4 as base make this method attractive for applications on an industrial scale.
114 citations
Cited by
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TL;DR: Using R-Hydroxy Stannanes as a Model for a Methylenation Reaction and Conclusions and Future Prospects are presented.
Abstract: 6.4. Polyynes 3123 6.5. Using R-Hydroxy Stannanes 3124 6.6. Using the Hurtley Reaction 3124 6.7. Using a Methylenation Reaction 3125 7. Conclusions and Future Prospects 3125 8. Uncommon Abbreviations 3125 9. Acknowledgments 3125 10. Note Added in Proof 3125 11. References 3126 * Authorstowhomcorrespondenceshouldbeaddressed(evano@chimie.uvsq.fr, nicolas.blanchard@uha.fr). † Université de Versailles Saint Quentin en Yvelines. ‡ Université de Haute-Alsace. Chem. Rev. 2008, 108, 3054–3131 3054
1,789 citations
1,566 citations
TL;DR: An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.
Abstract: Copper-catalyzed Ullmann condensations are key reactions for the formation of carbon-heteroatom and carbon-carbon bonds in organic synthesis. These reactions can lead to structural moieties that are prevalent in building blocks of active molecules in the life sciences and in many material precursors. An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.
1,458 citations
1,326 citations
TL;DR: This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
Abstract: 140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
1,141 citations