Christian Bruneau

article

Ruthenium Catalyzed Regioselective β‐C(sp³)−H Functionalization of N‐Alkyl‐N′‐p–nitrophenyl Substituted Piperazines using Aldehydes as Alkylating Agents

V. Murugesh, Apurba Ranjan Sahoo, Mathieu Achard, Gangavaram V. M. Sharma, more

Advanced Synthesis & Catalysis > 363 > 2 > 453 - 458

Herein, we disclose a ruthenium‐catalyzed regioselective β‐C(sp³)−H bond functionalization on the piperazine core using aldehydes as alkylating agents. The present transformation appears to go through the dehydrogenation of the piperazine to propagate to enamine in situ, followed by nucleophilic addition to the aldehyde and hydrogenation to result in the regioselective β‐C(sp³)−H alkylation. A variety...

article

Acceptorless and Base‐Free Dehydrogenation of Alcohols Mediated by a Dipyridylamine‐Iridium(III) Catalyst

Harikrishnan Jayaprakash, Liwei Guo, Shengdong Wang, Christian Bruneau, more

European Journal of Organic Chemistry > 2020 > 28 > 4326 - 4330

Several dipyridylamine‐Ir^III and dipyridylamine‐Ru^II complexes have been evaluated in the acceptorless dehydrogenation of alcohols in the absence of base additives. Iridium catalysts were found superior to ruthenium complexes, and the nature of the bridging nitrogen in dipyridylamine ligands was also evidenced as a key parameter. Catalytic reactions were conducted in toluene, but more sustainable...

article

Investigation of hybrid‐capacitor properties of ruthenium complexes

Serdar Altin, Erdinç Öz, Sebahat Altundağ, Ali Bayri, more

International Journal of Energy Research > 43 > 13 > 6840 - 6851

Ru complexes were successfully produced, and their structural properties were investigated using FTIR, Raman, and single crystal XRD patterns. The HOMO, LUMO, Eg, and electronic surface potential (ESP) values of the molecules were calculated by a Gaussian program. The complexes were used for producing hybrid capacitor cells as electrode materials. According to electrochemical analysis, complex 2 showed...

article

Ruthenium(II)‐(Arene)‐N‐Heterocyclic Carbene Complexes: Efficient and Selective Catalysts for the N‐Alkylation of Aromatic Amines with Alcohols

Nazan Kaloğlu, Mathieu Achard, Christian Bruneau, İsmail Özdemir

European Journal of Inorganic Chemistry > 2019 > 21 > 2598 - 2606

A series of unsymmetrical 1,3‐disubstituted benzimidazolium chlorides were synthesized as N‐heterocyclic carbene (NHC) precursors. These compounds were used for synthesis of the new ruthenium(II) complexes of the type [RuCl₂(arene)(NHC)], (arene = η⁶‐p‐cymene). The structures of all compounds were characterized by ¹H NMR, ¹³C NMR and FT‐IR spectroscopy techniques. The catalytic activity of the ruthenium...

article

Silver‐Catalyzed Hydrogenation of Ketones under Mild Conditions

Shengdong Wang, Haiyun Huang, Svetlana Tsareva, Christian Bruneau, more

Advanced Synthesis & Catalysis > 361 > 4 > 786 - 790

The silver‐catalyzed hydrogenation of ketones using H₂ as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields. This silver catalyst allows for the selective hydrogenation of ketones...

article

First elaboration of an olefin metathesis catalytic membrane by grafting a Hoveyda–Grubbs precatalyst on zirconia membranes

Adel Keraani, Murielle Rabiller-Baudry, Cédric Fischmeister, David Delaunay, more

Comptes Rendus Chimie > 2017 > 20 > 9-10 > 952-966

This study is aimed at developing an innovative concept for the preparation of an olefin metathesis catalytic membrane. This goal was achieved by grafting a Grubbs II precatalyst on a zirconia membrane generating a tailor-made Hoveyda–Grubbs precatalyst on the surface of an ultrafiltration inorganic membrane. The obtained membranes were characterized by different techniques evidencing the grafting...

article

Synthesis of metathesis catalysts with fluorinated unsymmetrical N,N’-diaryl imidazoline-based NHC ligands

Salekh M. Masoud, Maxim A. Topchiy, Alexander S. Peregudov, Thierry Roisnel, more

Journal of Fluorine Chemistry > 2017 > 200 > C > 66-76

New olefin metathesis catalysts bearing unsymmetrical fluorinated NHC ligands with hexafluoroisopropylmethoxy group in ortho-positions of N-aryl-substituent have been synthesized. The effects of mono-ortho-arylsubstitution and the replacement of para-methyl N-aryl group with more electron-donating methoxy group in unsymmetrical fluorinated NHC ligand on the activity of complexes have been evaluated.

article

Syntheses and characterization of molecular weight enlarged olefin metathesis pre-catalysts

Adel Keraani, Ghassan Nasser, Saurabh Shahane, Thierry Renouard, more

Comptes Rendus Chimie > 2017 > 20 > 7 > 717-723

This study was aimed at developing a synthetic strategy of gradual increase in the steric bulk of ruthenium-based olefin metathesis pre-catalysts for organic solvent nanofiltration (OSN) processes. A series of five enlarged second-generation Hoveyda type pre-catalysts was prepared and characterized. The structural modifications were performed on the benzylidene ligand of an unmodified Hoveyda (II)...

article

Palladium‐Catalysed Cross‐Coupling Reactions Controlled by Noncovalent Zn⋅⋅⋅N Interactions

Mohamed Kadri, Jingran Hou, Vincent Dorcet, Thierry Roisnel, more

Chemistry – A European Journal > 23 > 21 > 5033 - 5043

Non‐covalent interactions between halopyridine substrates and catalytically inert building blocks, namely zinc(II)–porphyrins and zinc(II)–salphens, influence the catalytic outcome of Suzuki–Miyaura and Mizoroki–Heck palladium‐catalysed cross‐coupling reactions. The weak Zn⋅⋅⋅N interactions between halopyridine substrates and zinc(II)‐containing porphyrins and salphens, respectively, were studied...

article

Inside Back Cover: Palladium‐Catalysed Cross‐Coupling Reactions Controlled by Noncovalent Zn⋅⋅⋅N Interactions (Chem. Eur. J. 21/2017)

Mohamed Kadri, Jingran Hou, Vincent Dorcet, Thierry Roisnel, more

Chemistry – A European Journal > 23 > 21 > 5171 - 5171

Weak Zn⋅⋅⋅N interactions have been exploited in homogeneous palladium catalysis. The selective binding between pyridine‐containing compounds and zinc‐containing scaffolds (porphyrin or salphen) prevents undesired catalyst inhibition, thus increasing the activity of the palladium‐phosphane catalyst. The picture illustrates how a magician uses the “Zn⋅⋅⋅N weak interactions” trick to increase the performance...

article

PEPPSI‐Type Palladium–NHC Complexes: Synthesis, Characterization, and Catalytic Activity in the Direct C5‐Arylation of 2‐Substituted Thiophene Derivatives with Aryl Halides

Murat Kaloğlu, İsmail Özdemir, Vincent Dorcet, Christian Bruneau, more

European Journal of Inorganic Chemistry > 2017 > 10 > 1382 - 1391

Six benzimidazolium salts, having two nitrogen atoms substituted by various alkyl groups, have been synthesized in high yields. The benzimidazolium salts readily converted into the corresponding PEPPSI‐type palladium–NHC complexes (PEPPSI = pyridine‐enhanced precatalyst preparation, stabilization, and initiation). The structures of all compounds have been characterized by ¹H NMR, ¹³C NMR, and IR spectroscopy,...

article

One‐Pot Directing Group Formation/C−H Bond Functionalization via Copper(I) and Ruthenium(II) Catalysis

Christian Bruneau, Rafael Gramage‐Doria

Advanced Synthesis & Catalysis > 358 > 23 > 3847 - 3856

A copper(I)‐catalyzed oxidation leading to the formation of 2‐pyridyl ketone directing groups has been efficiently coupled with a ruthenium(II)‐catalyzed C(sp²)−H bond arylation transformation without performing any intermediate work‐up. This sustainable approach was further extended to sequential three‐step transition metal‐catalyzed transformations in which up to four new bonds (C–O, C–C, C–H and...

article

Nonconventional Supramolecular Self‐Assemblies of Zinc(II)–Salphen Building Blocks

Thomas Groizard, Samia Kahlal, Vincent Dorcet, Thierry Roisnel, more

European Journal of Inorganic Chemistry > 2016 > 32 > 5143 - 5151

In the presence of methanol (or ethanol) and acetone molecules, a zinc(II)–salphen [salphen = N,N′‐bis(3,5‐di‐tert‐butylsalicylidene)‐1,2‐phenylenediamine] building block gives rise to discrete supramolecular dimers involving both intermolecular hydrogen bonding and unique oxygen···oxygen interactions, that is, the O···O distances are much shorter than twice the van der Waals radius of an oxygen atom...

article

New fluorinated catalysts for olefin metathesis

Salekh M. Masoud, Artur K. Mailyan, Alexander S. Peregudov, Christian Bruneau, more

Mendeleev Communications > 2016 > 26 > 6 > 474-476

New olefin metathesis catalysts, analogues of Grubbs II ones, bearing hexafluoroisopropylmethoxy groups in NHC ligand, provide high conversions in model ring closing metathesis of diallylmalonate and cross metathesis of allylbenzene with 1,3-diacetoxybut-2-ene.

chapter

Cascade and Sequential Catalytic Transformations Initiated by Ruthenium Catalysts

Christian Bruneau, Sylvie Dérien, Pierre H. Dixneuf

Topics in Organometallic Chemistry > Metal Catalyzed Cascade Reactions > 295-326

Ruthenium holds a prominent position among the efficient transition metals involved in catalytic processes. Molecular ruthenium catalysts are able to perform unique transformations based on a variety of reaction mechanisms. They arise from easy to make complexes with versatile catalytic properties, and are ideal precursors for the performance of successive chemical transformations and catalytic reactions...

chapter

Ruthenium Vinylidenes and Allenylidenes in Catalysis

Christian Bruneau

Topics in Organometallic Chemistry > Ruthenium Catalysts and Fine Chemistry > 125-153

During the last decade, ruthenium catalysis, including asymmetric catalysis, has attracted increasing interest owing to its wide range of applications in organic synthesis [T. Naota, H. Takaya, S.I. Murahashi (1998) Chem. Rev. 98:2599; B.M. Trost, F.D. Toste, A.B. Pinkerton (2001) Chem. Rev. 101:2067; B.M. Trost BM (2002) Acc. Chem. Res. 35:695]. Ruthenium complexes bearing a carbenic ligand, such...

chapter

Ruthenium Vinylidenes and Allenylidenes in Catalysis

Christian Bruneau

Topics in Organometallic Chemistry > Ruthenium Catalysts and Fine Chemistry > 125-153

During the last decade, ruthenium catalysis, including asymmetric catalysis, has attracted increasing interest owing to its wide range of applications in organic synthesis [T. Naota, H. Takaya, S.I. Murahashi (1998) Chem. Rev. 98:2599; B.M. Trost, F.D. Toste, A.B. Pinkerton (2001) Chem. Rev. 101:2067; B.M. Trost BM (2002) Acc. Chem. Res. 35:695]. Ruthenium complexes bearing a carbenic ligand, such...

book

Ruthenium Catalysts and Fine Chemistry

Christian Bruneau, Pierre H. Dixneuf

Topics in Organometallic Chemistry

Molecular ruthenium catalysts, during the last decade, have provided new indispensable synthetic methods that cannot be promoted by other catalysts, and they now constitute an emerging field for the selective preparation of fine chemicals. The major reaction types for carbon-carbon and carbon-heteroatom bond formation, most of them with atom economy, are comprehensively discussed by leading experts...

book

Ruthenium Catalysts and Fine Chemistry

Christian Bruneau, Pierre H. Dixneuf

Topics in Organometallic Chemistry

Molecular ruthenium catalysts, during the last decade, have provided new indispensable synthetic methods that cannot be promoted by other catalysts, and they now constitute an emerging field for the selective preparation of fine chemicals. The major reaction types for carbon-carbon and carbon-heteroatom bond formation, most of them with atom economy, are comprehensively discussed by leading experts...

article

Benzimidazolium sulfonate ligand precursors and application in ruthenium-catalyzed aromatic amine alkylation with alcohols

Nazan Kaloglu, Ismail Özdemir, Nevin Gürbüz, Mathieu Achard, more

Catalysis Communications > 2016 > 74 > Complete > 33-38

New benzimidazolium sulfonate salts have been prepared and fully characterized. They have been associated in situ with [RuCl₂(p-cymene)]₂ to generate efficient catalytic systems operating at 120°C under neat conditions in the presence of potassium tert-butylate for selective N-alkylation of primary aromatic amines into secondary amines.

INFONA - science communication portal

Search results for: Christian Bruneau

Ruthenium Catalyzed Regioselective β‐C(sp³)−H Functionalization of N‐Alkyl‐N′‐p–nitrophenyl Substituted Piperazines using Aldehydes as Alkylating Agents

Acceptorless and Base‐Free Dehydrogenation of Alcohols Mediated by a Dipyridylamine‐Iridium(III) Catalyst

Investigation of hybrid‐capacitor properties of ruthenium complexes

Ruthenium(II)‐(Arene)‐N‐Heterocyclic Carbene Complexes: Efficient and Selective Catalysts for the N‐Alkylation of Aromatic Amines with Alcohols

Silver‐Catalyzed Hydrogenation of Ketones under Mild Conditions

First elaboration of an olefin metathesis catalytic membrane by grafting a Hoveyda–Grubbs precatalyst on zirconia membranes

Synthesis of metathesis catalysts with fluorinated unsymmetrical N,N’-diaryl imidazoline-based NHC ligands

Syntheses and characterization of molecular weight enlarged olefin metathesis pre-catalysts

Palladium‐Catalysed Cross‐Coupling Reactions Controlled by Noncovalent Zn⋅⋅⋅N Interactions

Inside Back Cover: Palladium‐Catalysed Cross‐Coupling Reactions Controlled by Noncovalent Zn⋅⋅⋅N Interactions (Chem. Eur. J. 21/2017)

PEPPSI‐Type Palladium–NHC Complexes: Synthesis, Characterization, and Catalytic Activity in the Direct C5‐Arylation of 2‐Substituted Thiophene Derivatives with Aryl Halides

One‐Pot Directing Group Formation/C−H Bond Functionalization via Copper(I) and Ruthenium(II) Catalysis

Nonconventional Supramolecular Self‐Assemblies of Zinc(II)–Salphen Building Blocks

New fluorinated catalysts for olefin metathesis

Cascade and Sequential Catalytic Transformations Initiated by Ruthenium Catalysts

Ruthenium Vinylidenes and Allenylidenes in Catalysis

Ruthenium Vinylidenes and Allenylidenes in Catalysis

Ruthenium Catalysts and Fine Chemistry

Ruthenium Catalysts and Fine Chemistry

Benzimidazolium sulfonate ligand precursors and application in ruthenium-catalyzed aromatic amine alkylation with alcohols

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