{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,29]],"date-time":"2026-01-29T21:30:27Z","timestamp":1769722227628,"version":"3.49.0"},"reference-count":149,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2017,4,4]],"date-time":"2017-04-04T00:00:00Z","timestamp":1491264000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003768","name":"Universit\u00e9 de Strasbourg","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003768","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004794","name":"Centre National de la Recherche Scientifique","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005856","name":"Faculdade de Ci\u00eancias e Tecnologia, Universidade Nova de Lisboa","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100005856","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2017,4,24]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Tri\u2010organyl and tricoordinate N\u2010heterocyclic carbene (NHC) Zn\u2013NHC alkyl cations [(<jats:italic>n<\/jats:italic>NHC)<jats:sub>2<\/jats:sub>Zn\u2010Me]<jats:sup>+<\/jats:sup> (<jats:italic>n<\/jats:italic>NHC=C2\u2010bonded\u2010IMes\/\u2010IDipp; <jats:bold>3<\/jats:bold><jats:sup>+<\/jats:sup> and <jats:bold>4<\/jats:bold><jats:sup>+<\/jats:sup>; IMes=1,3\u2010bis(2,4,6\u2010trimethylphenyl)imidazolin\u20102\u2010ylidene, IDipp=1,3\u2010bis(2,6\u2010diisopropylphenyl)imidazolin\u20102\u2010ylidene) were first synthesized and structurally characterized by ionization of the corresponding neutral precursors [(<jats:italic>n<\/jats:italic>NHC)ZnMe<jats:sub>2<\/jats:sub>] with [Ph<jats:sub>3<\/jats:sub>C][B(C<jats:sub>6<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>4<\/jats:sub>] in the presence of one equivalent of free NHC. Whereas cation [(<jats:italic>n<\/jats:italic>IMes)<jats:sub>2<\/jats:sub>Zn\u2010Me]<jats:sup>+<\/jats:sup> (<jats:bold>3<\/jats:bold><jats:sup>+<\/jats:sup>) is stable, its sterically congested analogue [(<jats:italic>n<\/jats:italic>IDipp)<jats:sub>2<\/jats:sub>Zn\u2010Me]<jats:sup>+<\/jats:sup> (<jats:bold>4<\/jats:bold><jats:sup>+<\/jats:sup>) readily undergoes an <jats:italic>n<\/jats:italic>NHC\u2010to\u2010<jats:italic>a<\/jats:italic>NHC isomerization in the presence of THF or IDipp to afford the more thermodynamically stable [(<jats:italic>a<\/jats:italic>IDipp)(<jats:italic>n<\/jats:italic>IDipp)Zn\u2010Me]<jats:sup>+<\/jats:sup> (<jats:italic>a<\/jats:italic>IDipp=C4\u2010bonded IDipp, <jats:bold>5<\/jats:bold><jats:sup>+<\/jats:sup>), reflecting the adaptable\u2010to\u2010sterics coordination chemistry of these cations for improved stability. Cations <jats:bold>3<\/jats:bold><jats:sup>+<\/jats:sup>\u2013<jats:bold>5<\/jats:bold><jats:sup>+<\/jats:sup> are the first Zn cations of the type Zn(C)(C\u2032)(C\u2032\u2032)<jats:sup>+<\/jats:sup> (C, C\u2032, C\u2032\u2032=<jats:italic>\u03c3<\/jats:italic>\u2010donor carbyl ligand). Kinetic studies combined with DFT calculations agree with an <jats:italic>n<\/jats:italic>NHC\u2010to\u2010<jats:italic>a<\/jats:italic>NHC process proceeding through the initial deprotonation of <jats:bold>4<\/jats:bold><jats:sup>+<\/jats:sup> (at a Zn\u2010bonded C4\u2010IDipp moiety) by IDipp. Unlike <jats:bold>3<\/jats:bold><jats:sup>+<\/jats:sup> and <jats:bold>4<\/jats:bold><jats:sup>+<\/jats:sup>, the rearranged cation <jats:bold>5<\/jats:bold><jats:sup>+<\/jats:sup> reacts with CO<jats:sub>2<\/jats:sub> through insertion into the Zn\u2013Me bond yielding the corresponding Zn(<jats:italic>\u03ba<\/jats:italic><jats:sup>2<\/jats:sup>\u2010OAc)<jats:sup>+<\/jats:sup> cation <jats:bold>6<\/jats:bold><jats:sup>+<\/jats:sup>. Both cations <jats:bold>5<\/jats:bold><jats:sup>+<\/jats:sup> and <jats:bold>6<\/jats:bold><jats:sup>+<\/jats:sup> were successfully used in CO<jats:sub>2<\/jats:sub> hydrosilylation catalysis for silylformate formation.<\/jats:p>","DOI":"10.1002\/chem.201605907","type":"journal-article","created":{"date-parts":[[2017,2,21]],"date-time":"2017-02-21T11:10:59Z","timestamp":1487675459000},"page":"5509-5519","source":"Crossref","is-referenced-by-count":50,"title":["N\u2010Heterocyclic Carbene Based Tri\u2010organyl\u2010Zn\u2013Alkyl Cations: Synthesis, Structures, and Use in CO<sub>2<\/sub> Functionalization"],"prefix":"10.1002","volume":"23","author":[{"given":"David","family":"Specklin","sequence":"first","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]},{"given":"Christophe","family":"Fliedel","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"},{"name":"LAQV, REQUIMTE, Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia Universidade Nova de Lisboa  2829-516 Caparica Portugal"}]},{"given":"Christophe","family":"Gourlaouen","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]},{"given":"Jean\u2010Charles","family":"Bruyere","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]},{"given":"Teresa","family":"Avil\u00e9s","sequence":"additional","affiliation":[{"name":"LAQV, REQUIMTE, Departamento de Qu\u00edmica, Faculdade de Ci\u00eancias e Tecnologia Universidade Nova de Lisboa  2829-516 Caparica Portugal"}]},{"given":"Corinne","family":"Boudon","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]},{"given":"Laurent","family":"Ruhlmann","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7393-286X","authenticated-orcid":false,"given":"Samuel","family":"Dagorne","sequence":"additional","affiliation":[{"name":"Institut de Chimie de Strasbourg, CNRS Universit\u00e9 de Strasbourg  1, rue Blaise Pascal 67000 Strasbourg France"}]}],"member":"311","published-online":{"date-parts":[[2017,4,4]]},"reference":[{"key":"e_1_2_7_1_1","first-page":"1","volume-title":"Comprehensive Organic Synthesis","author":"Hirose T.","year":"2014"},{"key":"e_1_2_7_2_1","unstructured":"For early reports on ZnIIalkyl cations 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CO2hydrosilylation and hydroboration:"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2015.06.003"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00055"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00428"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC01614A"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CY00948C"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc51070k"},{"key":"e_1_2_7_90_1","unstructured":"Recent representative examples of metal-based CO2hydrosilylation\/-boration catalysis :"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja103982t"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja305318c"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206165"},{"key":"e_1_2_7_93_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206165"},{"key":"e_1_2_7_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja308500s"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203226"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc41838c"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/om400175h"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309094"},{"key":"e_1_2_7_98_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309094"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC00885E"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic501901n"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CY00339J"},{"key":"e_1_2_7_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b06077"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b05692"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC06805G"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06319"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603524"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01497"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CY02139A"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6DT02135B"},{"key":"e_1_2_7_110_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2035706"},{"key":"e_1_2_7_111_1","unstructured":"For well-identified CO2insertion into a Zn\u2212H bond see also:"},{"key":"e_1_2_7_112_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc01329c"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CC36953B"},{"key":"e_1_2_7_114_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300749"},{"key":"e_1_2_7_114_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300749"},{"key":"e_1_2_7_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/om400679n"},{"key":"e_1_2_7_116_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501539"},{"key":"e_1_2_7_116_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501539"},{"key":"e_1_2_7_117_1","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.201400121"},{"key":"e_1_2_7_118_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18621230214"},{"key":"e_1_2_7_119_1","unstructured":"\u00a0"},{"key":"e_1_2_7_120_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000634"},{"key":"e_1_2_7_120_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000634"},{"key":"e_1_2_7_121_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900528h"},{"key":"e_1_2_7_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja803435w"},{"key":"e_1_2_7_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800764u"},{"key":"e_1_2_7_124_1","unstructured":"CO2insertion into a Cp\u2212Zn moiety is also known see:"},{"key":"e_1_2_7_125_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201100715"},{"key":"e_1_2_7_126_2","doi-asserted-by":"publisher","DOI":"10.1021\/om401000s"},{"key":"e_1_2_7_127_1","unstructured":"For NHC\u2212CO2zwitterionic adducts see:"},{"key":"e_1_2_7_128_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200801161"},{"key":"e_1_2_7_129_2","doi-asserted-by":"publisher","DOI":"10.1039\/b311350g"},{"key":"e_1_2_7_130_1","unstructured":"Though no apparent NHC dissociation is observed for cations3+and4+at room temperature the generation of free NHC (with subsequent formation of the corresponding NHC\u2212CO2adduct in the presence of CO2) cannot be excluded."},{"key":"e_1_2_7_131_1","unstructured":"Approximately 10\u2009% of the introduced silane HSi(OEt)3decomposed over time under catalytic conditions precluding a quantitative conversion to HCO2Si(OEt)3."},{"key":"e_1_2_7_132_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200806058"},{"key":"e_1_2_7_132_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200806058"},{"key":"e_1_2_7_133_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic501058j"},{"key":"e_1_2_7_134_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00040a007"},{"key":"e_1_2_7_135_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)00260-6"}],"container-title":["Chemistry \u2013 A European 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