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dc.contributor.authorQueval, Pierre
dc.contributor.authorJahier, Claire
dc.contributor.authorRouen, Mathieu
dc.contributor.authorArtur, Isabelle
dc.contributor.authorLegeay, Jean Christophe
dc.contributor.authorFalivene, Laura
dc.contributor.authorToupet, Loïc J.
dc.contributor.authorCrévisy, Christophe
dc.contributor.authorCavallo, Luigi
dc.contributor.authorBaslé, Olivier
dc.contributor.authorMauduit, Marc
dc.date.accessioned2015-08-03T11:36:45Z
dc.date.available2015-08-03T11:36:45Z
dc.date.issued2013-12-04
dc.identifier.citationQueval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2013). Multicomponent Synthesis of Unsymmetrical Unsaturated N-Heterocyclic Carbene Precursors and Their Related Transition-Metal Complexes. Angewandte Chemie International Edition, 52(52), 14103–14107. doi:10.1002/anie.201308873
dc.identifier.issn14337851
dc.identifier.doi10.1002/anie.201308873
dc.identifier.urihttp://hdl.handle.net/10754/563141
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.
dc.publisherWiley
dc.subjectchirality
dc.subjectligand design
dc.subjectmulticomponent reactions
dc.subjectN-heterocyclic carbenes
dc.subjecttransition metals
dc.titleMulticomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalAngewandte Chemie
dc.contributor.institutionEcole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France
dc.contributor.institutionInstitut de Physique de Rennes, Université Rennes 1, CNRS, UMR 6251, Rennes Cedex, France
dc.contributor.institutionDipartimento di Chimica, Università di Salerno, Fisciano, Italy
kaust.personCavallo, Luigi
dc.relation.issupplementedbyDOI:10.5517/cc1168gz
dc.relation.issupplementedbyDOI:10.5517/cc118dpd
dc.relation.issupplementedbyDOI:10.5517/cc118nml
dc.relation.issupplementedbyDOI:10.5517/cc10491h
dc.relation.issupplementedbyDOI:10.5517/cc106qb8
dc.relation.issupplementedbyDOI:10.5517/cc106whl
dc.relation.issupplementedbyDOI:10.5517/ccxyc28
dc.relation.issupplementedbyDOI:10.5517/ccxyc39
dc.relation.issupplementedbyDOI:10.5517/cc1095q6
dc.relation.issupplementedbyDOI:10.5517/ccz7n2x
dc.relation.issupplementedbyDOI:10.5517/ccz7x58
dc.relation.issupplementedbyDOI:10.5517/cczcbxk
dc.relation.issupplementedbyDOI:10.5517/cczxnxf
dc.relation.issupplementedbyDOI:10.5517/ccy3rj9
dc.relation.issupplementedbyDOI:10.5517/cc109xy5
dc.relation.issupplementedbyDOI:10.5517/cc10b4l2
dc.relation.issupplementedbyDOI:10.5517/cc10bcvk
dc.relation.issupplementedbyDOI:10.5517/cc10dblb
dc.relation.issupplementedbyDOI:10.5517/cc10fq6c
dc.relation.issupplementedbyDOI:10.5517/cc10j0p7
dc.relation.issupplementedbyDOI:10.5517/cc10jdnl
dc.relation.issupplementedbyDOI:10.5517/cc10qr5n
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc1168gz">10.5517/cc1168gz</a> HANDLE: <a href="http://hdl.handle.net/10754/624259">10754/624259</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc118dpd">10.5517/cc118dpd</a> HANDLE: <a href="http://hdl.handle.net/10754/624261">10754/624261</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc118nml">10.5517/cc118nml</a> HANDLE: <a href="http://hdl.handle.net/10754/624262">10754/624262</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10491h">10.5517/cc10491h</a> HANDLE: <a href="http://hdl.handle.net/10754/624194">10754/624194</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc106qb8">10.5517/cc106qb8</a> HANDLE: <a href="http://hdl.handle.net/10754/624199">10754/624199</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc106whl">10.5517/cc106whl</a> HANDLE: <a href="http://hdl.handle.net/10754/624200">10754/624200</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccxyc28">10.5517/ccxyc28</a> HANDLE: <a href="http://hdl.handle.net/10754/624672">10754/624672</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccxyc39">10.5517/ccxyc39</a> HANDLE: <a href="http://hdl.handle.net/10754/624673">10754/624673</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc1095q6">10.5517/cc1095q6</a> HANDLE: <a href="http://hdl.handle.net/10754/624203">10754/624203</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccz7n2x">10.5517/ccz7n2x</a> HANDLE: <a href="http://hdl.handle.net/10754/624752">10754/624752</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccz7x58">10.5517/ccz7x58</a> HANDLE: <a href="http://hdl.handle.net/10754/624753">10754/624753</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cczcbxk">10.5517/cczcbxk</a> HANDLE: <a href="http://hdl.handle.net/10754/624754">10754/624754</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cczxnxf">10.5517/cczxnxf</a> HANDLE: <a href="http://hdl.handle.net/10754/624767">10754/624767</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/ccy3rj9">10.5517/ccy3rj9</a> HANDLE: <a href="http://hdl.handle.net/10754/624684">10754/624684</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc109xy5">10.5517/cc109xy5</a> HANDLE: <a href="http://hdl.handle.net/10754/624204">10754/624204</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10b4l2">10.5517/cc10b4l2</a> HANDLE: <a href="http://hdl.handle.net/10754/624211">10754/624211</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10bcvk">10.5517/cc10bcvk</a> HANDLE: <a href="http://hdl.handle.net/10754/624212">10754/624212</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10dblb">10.5517/cc10dblb</a> HANDLE: <a href="http://hdl.handle.net/10754/624215">10754/624215</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10fq6c">10.5517/cc10fq6c</a> HANDLE: <a href="http://hdl.handle.net/10754/624216">10754/624216</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10j0p7">10.5517/cc10j0p7</a> HANDLE: <a href="http://hdl.handle.net/10754/624218">10754/624218</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10jdnl">10.5517/cc10jdnl</a> HANDLE: <a href="http://hdl.handle.net/10754/624219">10754/624219</a></li><li><i>[Dataset]</i> <br/> 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: <a href="https://doi.org/10.5517/cc10qr5n">10.5517/cc10qr5n</a> HANDLE: <a href="http://hdl.handle.net/10754/624235">10754/624235</a></li></ul>
dc.date.published-online2013-12-04
dc.date.published-print2013-12-23


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