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

Abstract

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.

Copper- and copper– N -heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO 2 at ambient conditions

“…Copper catalysts can also catalyze various C─H and C-halogen activation reactions, and many of them involve intermediates with a Cu─C bond (36)(37)(38). These facts make copper catalysts a very promising choice for CO 2 transformation, especially with the formation of new C─C bonds.…”

Theoretical Investigations on Deactivation of Copper Catalytic Species in Ullmann Cross Coupling Reactions

“…These reactions are essential tool in modern laboratories and industries for the synthesis of bio-active drugs, agro-chemicals and polymers [5,[6][7][8]. Copper mediated reactions have many advantages over palladium mediated reactions, like overall low cost, simple ligands and eco-friendly process [9]. Classical Ullamann coupling reactions had certain limitations, reaction conditions could be revitalized by introduction of N,N/N,O/O,O ligands and inorganic bases [10].…”

Microwave-assisted Cu-catalyzed Ullmann ether synthesis in a continuous-flow milli-plant

“…The Ullmann-type C-C, C-O and C-N coupling reactions, discovered more than a century ago by Ullmann and Goldberg, have recently encountered a renaissance, mainly as a result of the exploitation of highly efficient copper-based catalysts [44][45][46][47][48][49][50][51][52]. However, these Ullmanntype coupling reactions still suffer from the need for harsh reaction conditions, the use of high levels of catalyst (50-100 mol%) and also the need to use relatively reactive and expensive aryl halides.…”