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Lamblin M.,University of Bordeaux Segalen | Nassar-Hardy L.,CNRS Institute of Molecular Sciences | Hierso J.-C.,CNRS Molecular Chemistry Institute of Burgundy University | Fouquet E.,CNRS Institute of Molecular Sciences | Felpin F.-X.,CNRS Institute of Molecular Sciences
Advanced Synthesis and Catalysis

This review summarizes the progress made essentially these last ten years on heterogeneous palladium catalysis in pure water. The work covers four important palladium-catalyzed transformations for carbon-carbon bond formation: Suzuki, Heck, Sonogashira and Tsuji-Trost reactions. The discussion focuses on the efficiency and reusability of the heterogeneous catalysts as well as on the experimental conditions from a sustainable chemistry point of view. The review is introduced by a discussion on mechanistic aspects inherent to heterogeneous catalysis. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. Source

Bertrand B.,University of Groningen | Bertrand B.,CNRS Molecular Chemistry Institute of Burgundy University | Casini A.,University of Groningen
Dalton Transactions

From wedding rings on fingers to stained glass windows, by way of Olympic medals, gold has been highly prized for millennia. Nowadays, organometallic gold compounds occupy an important place in the field of medicinal inorganic chemistry due to their unique chemical properties with respect to gold coordination compounds. In fact, several studies have proved that they can be used to develop highly efficient metal-based drugs with possible applications in the treatment of cancer. This Perspective summarizes the results obtained for different families of bioactive organometallic gold compounds including cyclometallated gold(iii) complexes with C,N-donor ligands, gold(i) and gold(i/iii) N-heterocyclic (NHC) carbene complexes, as well as gold(i) alkynyl complexes, with promising anticancer effects. Most importantly, we will focus on recent developments in the field and discuss the potential of this class of organometallic compounds in relation to their versatile chemistry and innovative mechanisms of action. © 2014 The Royal Society of Chemistry. Source

Among the most common high-resolution nuclear magnetic resonance parameters (NMR parameters), nuclear spin-spin coupling provides decisive data for organic, organometallic, biological and coordination compounds characterization. This electron-mediated coupling characterized by J constant is very classically thought as transmitted by unambiguously covalently bonded atoms. Yet, experimental and theoretical NMR studies have highlighted since the sixties the existence of scalar J spin couplings operating via clearly nonbonded interactions, these couplings are often called "through-space" internuclear spin-spin couplings (TS couplings). We discovered that the through-space spin coupling was not only a phenomenon detectable in fluorinated constrained organic molecules, but also in organometallic and coordinating compounds, and especially in palladium and group 10 coordination complexes of constrained polyphosphine ligands. The present article aims at revealing the TS contribution of indirect nuclear spin-spin in ferrocenyl polyphosphine and their palladium coordination complexes. Theoretical and fundamental aspects are introduced in continuous relationship with experimental spectroscopic and structural data. The role of lone-pairs in nonbonded spin-spin coupling is disclosed and correlated with through-space distance dependence of J constant intensity within palladium and nickel halide complexes. Some important consequences in structural characterization of the compounds in solution are discussed. The spatial proximity of phosphorus atoms - recognized from TS spin couplings - is at the origin of new reactivity and mechanistic understanding in C-C palladium-catalyzed cross-coupling, which are quoted herein. Future trends in the modelling of this fascinating phenomenon, towards a better understanding, are briefly evoked. © 2011 Bentham Science Publishers. Source

Picquet M.,CNRS Molecular Chemistry Institute of Burgundy University
Platinum Metals Review

The article presents the state-of-the-art in the industrial use of organometallic or coordination complexes as catalysts for the production of fine chemicals. Extensively reviewed by Johannes G. de Vries (DSM Innovative Synthesis BV, Geleen, The Netherlands) in the first chapter, palladium-catalyzed coupling reactions appear to be among the most popular reactions for the production of fine chemicals at the ton-scale. Provided inhibition and deactivation of the catalyst is avoided, catalytic C-C coupling may offer several advantages such as total cost reduction, tolerance to many functional groups and lower reaction temperatures. Asymmetric hydroformylation is a powerful tool to introduce chirality in pharmaceuticals. However, it has remained so far a purely academic domain with no industrial-scale application. Source

Platon M.,CNRS Molecular Chemistry Institute of Burgundy University | Amardeil R.,CNRS Molecular Chemistry Institute of Burgundy University | Djakovitch L.,CNRS Research on Catalysis and Environment in Lyon | Hierso J.-C.,CNRS Molecular Chemistry Institute of Burgundy University
Chemical Society Reviews

A survey highlighting the most recent palladium catalytic systems produced and their performances for progress in direct synthesis of indole backbones by heterocarbocyclization of reactive substrates is provided. The discussion is developed in relation with the principles of sustainable chemistry concerning atom and mass economy. In this respect, the general convergent character of the syntheses is of particular interest (one-pot, domino, cascade or tandem reactions), and the substrates accessibility and reactivity, together with the final waste production, are also important. This critical review clearly indicates that the development of ligand chemistry, mainly phosphines and carbenes, in the last few decades gave a significant impetus to powerful functionalization of indoles at virtually all positions of this ubiquitous backbone (118 references). © 2012 The Royal Society of Chemistry. Source

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