Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Handle URI:
http://hdl.handle.net/10754/563141
Title:
Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes
Authors:
Queval, Pierre; Jahier, Claire; Rouen, Mathieu; Artur, Isabelle; Legeay, Jean Christophe; Falivene, Laura; Toupet, Loïc J.; Crévisy, Christophe; Cavallo, Luigi ( 0000-0002-1398-338X ) ; Baslé, Olivier; Mauduit, Marc
Abstract:
A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
4-Dec-2013
DOI:
10.1002/anie.201308873
Type:
Article
ISSN:
14337851
Is Supplemented By:
Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 959340: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1168gz; DOI:10.5517/cc1168gz; HANDLE:http://hdl.handle.net/10754/624259; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 961393: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc118dpd; DOI:10.5517/cc118dpd; HANDLE:http://hdl.handle.net/10754/624261; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 961639: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc118nml; DOI:10.5517/cc118nml; HANDLE:http://hdl.handle.net/10754/624262; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 927645: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10491h; DOI:10.5517/cc10491h; HANDLE:http://hdl.handle.net/10754/624194; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 929979: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc106qb8; DOI:10.5517/cc106qb8; HANDLE:http://hdl.handle.net/10754/624199; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 930139: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc106whl; DOI:10.5517/cc106whl; HANDLE:http://hdl.handle.net/10754/624200; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 862360: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxyc28; DOI:10.5517/ccxyc28; HANDLE:http://hdl.handle.net/10754/624672; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 862361: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxyc39; DOI:10.5517/ccxyc39; HANDLE:http://hdl.handle.net/10754/624673; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 932347: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1095q6; DOI:10.5517/cc1095q6; HANDLE:http://hdl.handle.net/10754/624203; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 901079: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccz7n2x; DOI:10.5517/ccz7n2x; HANDLE:http://hdl.handle.net/10754/624752; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 901330: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccz7x58; DOI:10.5517/ccz7x58; HANDLE:http://hdl.handle.net/10754/624753; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 904639: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczcbxk; DOI:10.5517/cczcbxk; HANDLE:http://hdl.handle.net/10754/624754; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 921286: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczxnxf; DOI:10.5517/cczxnxf; HANDLE:http://hdl.handle.net/10754/624767; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 867551: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccy3rj9; DOI:10.5517/ccy3rj9; HANDLE:http://hdl.handle.net/10754/624684; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933067: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc109xy5; DOI:10.5517/cc109xy5; HANDLE:http://hdl.handle.net/10754/624204; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933273: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10b4l2; DOI:10.5517/cc10b4l2; HANDLE:http://hdl.handle.net/10754/624211; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933498: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10bcvk; DOI:10.5517/cc10bcvk; HANDLE:http://hdl.handle.net/10754/624212; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 935381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10dblb; DOI:10.5517/cc10dblb; HANDLE:http://hdl.handle.net/10754/624215; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 936702: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10fq6c; DOI:10.5517/cc10fq6c; HANDLE:http://hdl.handle.net/10754/624216; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 938918: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10j0p7; DOI:10.5517/cc10j0p7; HANDLE:http://hdl.handle.net/10754/624218; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 939289: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10jdnl; DOI:10.5517/cc10jdnl; HANDLE:http://hdl.handle.net/10754/624219; Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 945381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10qr5n; DOI:10.5517/cc10qr5n; HANDLE:http://hdl.handle.net/10754/624235
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorQueval, Pierreen
dc.contributor.authorJahier, Claireen
dc.contributor.authorRouen, Mathieuen
dc.contributor.authorArtur, Isabelleen
dc.contributor.authorLegeay, Jean Christopheen
dc.contributor.authorFalivene, Lauraen
dc.contributor.authorToupet, Loïc J.en
dc.contributor.authorCrévisy, Christopheen
dc.contributor.authorCavallo, Luigien
dc.contributor.authorBaslé, Olivieren
dc.contributor.authorMauduit, Marcen
dc.date.accessioned2015-08-03T11:36:45Zen
dc.date.available2015-08-03T11:36:45Zen
dc.date.issued2013-12-04en
dc.identifier.issn14337851en
dc.identifier.doi10.1002/anie.201308873en
dc.identifier.urihttp://hdl.handle.net/10754/563141en
dc.description.abstractA low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en
dc.publisherWiley-Blackwellen
dc.subjectchiralityen
dc.subjectligand designen
dc.subjectmulticomponent reactionsen
dc.subjectN-heterocyclic carbenesen
dc.subjecttransition metalsen
dc.titleMulticomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionEcole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, Franceen
dc.contributor.institutionInstitut de Physique de Rennes, Université Rennes 1, CNRS, UMR 6251, Rennes Cedex, Franceen
dc.contributor.institutionDipartimento di Chimica, Università di Salerno, Fisciano, Italyen
kaust.authorCavallo, Luigien
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