CNRS Laboratory of Molecular and Thio-Organic Chemistry

Caen, France

CNRS Laboratory of Molecular and Thio-Organic Chemistry

Caen, France
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Dupre J.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Gaumont A.-C.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Lakhdar S.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Organic Letters | Year: 2017

Frustrated Lewis pair (FLP)-catalyzed reduction of Michael acceptors is a challenging reaction that proceeds with specific FLP structures. Kinetics and equilibrium of the reactions of two phosphines (Ar3P), namely tri(1-naphthyl)phosphine and tri(o-tolyl)phosphine, are reported with reference electrophiles. The reason for the failure of the FLPs (Ar3P/B(C6F5)3) to reduce activated alkenes under H2 pressure is shown to be a hydrophosphination process that inhibits the reduction reaction. Kinetic and thermodynamic factors controlling both pathways are discussed in light of Mayr's free linear energy relationships. © 2017 American Chemical Society.


Renaud J.-L.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Gaillard S.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Topics in Organometallic Chemistry | Year: 2015

The formation of carbon–heteroatom bonds (C–X bonds with X¼N, S, P) upon addition of X-nucleophiles or X-electrophiles to unsaturated alkynes and alkenes, cross-coupling reactions, cycloadditions, tandem or consecutive reactions, or C–H functionalization is an attractive strategy in organic synthesis and is an intensive research area. Many organometallic species, more specifically palladium, nickel, and rhodium complexes, have paved the way to useful synthetic applications in this field. This chapter will cover iron-catalyzed bond-forming reactions between carbon and a heteroatom. © Springer International Publishing Switzerland 2015.


Aubin Y.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Fischmeister C.,CNRS Chemistry Institute of Rennes | Thomas C.M.,Chimie Paristech | Renaud J.-L.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Chemical Society Reviews | Year: 2010

The traditional homogeneous access to aromatic amine derivatives is a nucleophilic aromatic substitution of the corresponding aryl halides. The halogen atom is usually relatively inert to amination reaction unless it is activated by the presence of electron withdrawing groups. Consequently, there has been particular emphasis over the past decade on the synthesis of metal complexes that are active catalysts for the preparation of aromatic amines. This tutorial review focuses on the use of metal-based complexes for the direct amination of aryl halides with ammonia. © 2010 The Royal Society of Chemistry.


Pagnoux-Ozherelyeva A.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Pannetier N.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Mbaye M.D.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Mbaye M.D.,University of Ziguinchor | And 2 more authors.
Angewandte Chemie - International Edition | Year: 2012

An aminated series: A well-defined iron-catalyzed reductive amination reaction of aldehydes and ketones with aliphatic amines using molecular hydrogen is presented. Under mild conditions, good yields for a broad range of alkyl ketones as well as aldehydes were achieved. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Make O.,INSA Rouen | Dez I.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Levacher V.,INSA Rouen | Briere J.-F.,INSA Rouen
Angewandte Chemie - International Edition | Year: 2010

All paired up: Under catalytic phase-transfer conditions the formation of a chiral ion pair between quininium cation 1 and hydrazine anion 2 led to an enantioselective aza-Michael cyclocondensation domino reaction to furnish pyrazolines. A convenient one-pot protocol allowed exchange of the functional group (R1) on the nitrogen atom. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.


Elmkaddem M.K.,CNRS Chemistry Institute of Rennes | Fischmeister C.,CNRS Chemistry Institute of Rennes | Thomas C.M.,École Nationale Supérieure de Chimie de Paris | Renaud J.-L.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Chemical Communications | Year: 2010

A copper(i) catalyzed amination reaction utilizing aqueous ammonia and operating under mild conditions is presented. This method was employed for the efficient synthesis of various aminopyridine derivatives bearing electron withdrawing and electron donating groups. © The Royal Society of Chemistry 2010.


Welsch T.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Tran H.-A.,University of Alberta | Witulski B.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Organic Letters | Year: 2010

The combination of a modular assembly of enantiopure triynes and a powerful rhodium-catalyzed [2 + 2 + 2] alkyne cyclotrimerization reaction opens new and efficient entries to a set of alcyopterosins, including the first total synthesis of the alcyopterosins L, M, and C. © 2010 American Chemical Society.


Jouvin K.,University of Versailles | Veillard R.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Theunissen C.,Roosevelt University | Alayrac C.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | And 2 more authors.
Organic Letters | Year: 2013

An original and user-friendly synthesis of alkynylphosphine-boranes, useful building blocks in organic synthesis, based on an oxidative P-alkynylation reaction with readily available copper acetylides is reported. The ability of a secondary phosphine protected with a borane to undergo oxidative coupling without oxidation of the P-moiety is demonstrated for the first time. The reaction, which proceeds at room temperature, is applicable to the preparation of enantioenriched and structurally complex alkynylphosphine-boranes. © 2013 American Chemical Society.


Bernoud E.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Alayrac C.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Delacroix O.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Gaumont A.-C.,CNRS Laboratory of Molecular and Thio-Organic Chemistry
Chemical Communications | Year: 2011

A new and smooth approach towards alkynylphosphine derivatives is described. It relies on the unprecedented catalytic coupling of secondary phosphine boranes with alkynyl bromides using the CuI/1,10-phenanthroline couple. © 2011 The Royal Society of Chemistry.


Dassonneville B.,Johannes Gutenberg University Mainz | Witulski B.,CNRS Laboratory of Molecular and Thio-Organic Chemistry | Detert H.,Johannes Gutenberg University Mainz
European Journal of Organic Chemistry | Year: 2011

The total syntheses of the carboline alkaloids perlolyrine and "isoperlolyrine" are reported. Key-steps of the syntheses are Negishi coupling reactions on alkynylynamides and their metal-catalyzed [2+2+2] cycloadditions with nitriles to form the β- and γ-carboline cores. The choice of the catalyst strongly affects the β/γ ratio. Spectroscopic features of the γ-isomer are distinctly different from those of the naturally occurring isoperlolyrine. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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