UFU (‘Ullmann–Finkelstein–Ullmann’): a new multicomponent reaction

Toto, Patrick; Gesquière, Jean‐Claude; Cousaert, Nicolas; Deprez, Benoı̂t; Willand, Nicolas

doi:10.1016/j.tetlet.2006.04.041

Cited by 28 publications

(9 citation statements)

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“…By heating a mixture of aryl bromide and sodium iodide (2 equiv) in dioxane at 110 °C in the presence of 5 mol % of copper(I) iodide and 10 mol % of diamine ligand L4 , a smooth transformation of arylbromides to the corresponding iodides occurs in yields >93% (Scheme ) . Two examples with vinyl bromides have been reported, , and the method has found applications for in situ generation of aryl iodides, which can then undergo copper-mediated transformations, , as well as for an Ullmann−Finkelstein−Ullmann multicomponent reaction yielding unsymmetrical p -diaminobenzenes …”

Section: Background: Copper-mediated Coupling Reactionsmentioning

confidence: 99%

Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

2008

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Gwilherm Evano studied chemistry at the Ecole Normale Supe ´rieure in Paris (France) and received his Ph.D. from Universite ´Pierre et Marie Curie in 2002 under the supervision of Franc ¸ois Couty and Claude Agami. After postdoctoral study with James S. Panek at Boston University, working on the total synthesis of the ansamycin natural products Cytotrienin A and Reblastatin, he joined the CNRS as Charge ´de Recherche at the University of Versailles in 2004. His research interests focus on asymmetric synthesis and reactivity of nitrogen heterocycles, copper-catalyzed cyclization reactions, and the total synthesis of natural products. Nicolas Blanchard obtained his Ph.D. in 2000 from Paris VI University (France) under the supervision of Professor J. Cossy and Dr. C. Meyer, working on the total synthesis of the ionophoric antibiotic zincophorin. He then joined Professor W. R. Roush (University of Michigan) for a postdoctoral stay (2001-2002) as a Lavoisier fellow, working on the total synthesis of the plecomacrolide formamicin. In late 2002, he joined the CNRS as Charge ´de Recherche in Professor Kouklovsky's laboratory (Orsay University, France). In 2006, he moved to the group of Prof. J. Eustache (Haute-Alsace University, France). His research interests focus on the synthesis of biologically relevant compounds using new methodologies including nitroso Diels-Alder cycloadditions and stereoselective metalmediated transformations.

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Section: Background: Copper-mediated Coupling Reactionsmentioning

confidence: 99%

Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

2008

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“…A copper-mediated halogen-exchange of this type was recently 40 employed in a three-component reaction sequence for the synthesis of 1,4-diamidobenzenes. 27 There is also a single report of copper-mediated fluorination by reaction of 2-bromonitrobenzene with potassium fluoride and the Copper(I) complex (Ph 3 P) 3 CuF (Scheme 7). 28 The 45 reaction is apparently not just a simple S N Ar process as reaction with KF under the same conditions led to very low yields of the fluorobenzene.…”

Section: Possible Mechanismsmentioning

confidence: 99%

Metal-catalysed halogen exchange reactions of aryl halides

Sheppard

2009

Org. Biomol. Chem.

119

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Aryl halides are common synthetic targets themselves, and also highly versatile synthetic intermediates. Aryl chlorides are much more widely available and easier to synthesise than the other halide derivatives, so the development of effective methods for interconverting aryl halide derivatives would therefore be extremely useful. This article outlines which transformations are particularly desirable, and describes the progress that has been made on developing methods for carrying out those transformations using copper, nickel or palladium catalysts. The possible mechanisms of these reactions are discussed, with a view to identifying areas for future investigation.

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“…The first step in the synthetic sequences for 98 – 100 was introducing their central anilino-N bonds. These bonds in precursors 89 , 92 , and 93 were generated in respective yields of 78, 65, and 69% by the palladium-catalyzed coupling of 84 and 85 with 86 (the precursor of 25 ) and the copper(I)-catalyzed coupling of 87 with the phenyl iodide 88 , respectively. The side chains of 98 and 100 were introduced next.…”

Section: Resultsmentioning

confidence: 99%

Heteroatom-Substituted Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic Acid

et al. 2011

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(E)-4-[3'-(1-Adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell cycle arrest and apoptosis of cancer cells. Because its pharmacologic properties-solubility, bioavailability, and toxicity-required improvement for translation, structural modifications were made by introducing nitrogen atoms into the cinnamyl ring and replacing its E-double bond with XCH(2) (X = O, N, and S) with the objective of enhancing these properties without impacting apoptosis-inducing activity. Analogues having nitrogen atoms in heterocyclic rings corresponding to the cinnamyl phenyl ring displayed equal or higher biological activities. The pyrimidine and pyridine analogues were more soluble in both phosphate-buffered saline and water. While the 2,5-disubstituted pyridine analogue was the most potent inducer of KG-1 acute myeloid leukemia cell apoptosis, on the basis of apoptotic activity in KG-1 cells and solubility, the 2,5-disubstituted pyrimidine proved to be the more promising candidate for treatment of acute myeloid leukemia.

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UFU (‘Ullmann–Finkelstein–Ullmann’): a new multicomponent reaction

Cited by 28 publications

References 10 publications

Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis

Metal-catalysed halogen exchange reactions of aryl halides

Heteroatom-Substituted Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic Acid

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