Saint-Pierre-du-Chemin, France
Saint-Pierre-du-Chemin, France

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Pehlivan L.,University Claude Bernard Lyon 1 | Metay E.,University Claude Bernard Lyon 1 | Laval S.,University Claude Bernard Lyon 1 | Dayoub W.,University Claude Bernard Lyon 1 | And 3 more authors.
European Journal of Organic Chemistry | Year: 2011

An efficient reduction of aromatic and aliphatic esters with 1,1,3,3-tetramethyldisiloxane in combination with [MoO 2(acac) 2] or [V(O)(OiPr) 3] is reported. In the former system, the presence of triphenylphosphane oxide allows high conversion and good isolated yield to be reached. For the latter system, no ligand is necessary to obtain the corresponding alcohols with similar results. 1,1,3,3-Tetramethyldisiloxane in association with [MoO 2(acac) 2] or [V(O)(OiPr) 3] was found to efficiently reduce aliphatic and aromatic esters. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | And 5 more authors.
Tetrahedron | Year: 2014

1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction. © 2013 Elsevier Ltd. All rights reserved.


Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | And 3 more authors.
Tetrahedron Letters | Year: 2014

A simple and convenient method for the chemoselective reduction of nitriles into aldehydes using a 1,1,3,3-tetramethyldisiloxane (TMDS)/ triisopropoxyvanadium(V) oxide reducing system is described. Aromatic as well as aliphatic nitriles are reduced into the corresponding aldehydes in moderate to good yields. © 2013 Elsevier Ltd. All rights reserved.


Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Boyron O.,French National Center for Scientific Research | Demonchaux P.,Minakem SAS | And 2 more authors.
European Journal of Organic Chemistry | Year: 2011

The 1, 1, 3, 3-tetramethyldisiloxane/Pd/C system is reported here as a new method to accomplish the ring-opening of ethers and epoxides to give protected alcohols. The approach can also be used for the protection of primary or secondary alcohols and for the reduction of aldehydes and ketones to obtain alkoxysilanes. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | And 5 more authors.
Tetrahedron Letters | Year: 2011

A simple and useful method for the reduction of primary amides into the corresponding amines using a polymethylhydrosiloxane (PMHS)-Ti(OiPr) 4 reducing system is described. Aromatic as well as aliphatic primary amides are reduced in high selectivity and excellent yields. The reduction could proceed via dehydration of the primary amide group into the corresponding nitrile which is then reduced into the corresponding primary amine. © 2011 Elsevier Ltd. All rights reserved.


Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | And 3 more authors.
Tetrahedron | Year: 2011

The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac) 3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained. © 2011 Elsevier Ltd. All rights reserved.


Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Delbrayelle D.,Minakem SAS | Mignani G.,Rhodia | Lemaire M.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry
European Journal of Organic Chemistry | Year: 2012

An efficient reduction followed by cyclization of diacid compounds with the InBr 3/TMDS system is reported. This system allows the formation of five- and six-membered ring ethers substituted in the 3- or 4-position. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | And 3 more authors.
Tetrahedron Letters | Year: 2010

An efficient reduction of the nitro group with a catalytic amount of Fe(acac) 3 and TMDS in THF at 60 °C affording the corresponding amine is described. © 2010 Elsevier Ltd. All rights reserved.


Joncour R.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Duguet N.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Ferreira A.,Minakem SAS | Lemaire M.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry
Green Chemistry | Year: 2014

A direct synthesis of paracetamol (acetaminophen) from hydroquinone has been developed using ammonium acetate as an amidating agent. The reaction proceeds in acetic acid at elevated temperatures without any metallic catalyst. Under these conditions, paracetamol was obtained with high yield and selectivity (>95%). The reaction has also been carried out on the multi-gram scale (44 g of hydroquinone) and a potential process has been proposed based on the recycling of the solvent and by-products. This amidation protocol has also been extended to other phenol derivatives. This journal is © the Partner Organisations 2014.


Pehlivan L.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Metay E.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Delbrayelle D.,Minakem SAS | Mignani G.,Rhodia | Lemaire M.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry
Tetrahedron | Year: 2012

An efficient method for the reduction of phosphine oxide derivatives into their corresponding phosphines is described. The system InBr 3/TMDS allows the reduction of different secondary and tertiary phosphine oxides as well as aliphatic and aromatic phosphine oxides. © 2012 Elsevier Ltd. All rights reserved.

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