{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T00:53:52Z","timestamp":1785459232369,"version":"3.56.0"},"reference-count":87,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2018,2,15]],"date-time":"2018-02-15T00:00:00Z","timestamp":1518652800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,3,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The first C5\u2010protonated abnormal N\u2010heterocyclic carbene (aNHC), PhC{N(2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>)}<jats:sub>2<\/jats:sub>CHC: (<jats:bold>4<\/jats:bold>) is readily accessible by C4\u2010deprotonation of [ArC{N(2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>)}<jats:sub>2<\/jats:sub>CHCH]X (<jats:bold>3\u2009a<\/jats:bold>\u2010X) (Ar=Ph, X=Br or I) with a base. The aNHC <jats:bold>4<\/jats:bold> is stable at 298\u2005K in [D<jats:sub>8<\/jats:sub>]THF solution and has been spectroscopically characterized. The facile availability of <jats:bold>4<\/jats:bold> enables the synthesis of a series of main\u2010group compounds as well as transition\u2010metal complexes featuring a new phosphorus\u2010aNHC hybrid ligand. Double deprotonation of [ArC{N(2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>)}<jats:sub>2<\/jats:sub>CHCH]X (Ar=Ph, <jats:bold>3\u2009a<\/jats:bold>\u2010X (X=Br or I); 4\u2010Tol, <jats:bold>3\u2009b<\/jats:bold>\u2010Br; 4\u2010DMP, <jats:bold>3\u2009c<\/jats:bold>\u2010Br; Tol=MeC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>, DMP=Me<jats:sub>2<\/jats:sub>NC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>) with <jats:italic>n<\/jats:italic>BuLi yields the C4,C5\u2010ditopic carbanionic aNHCs, [ArC{N(2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>)}<jats:sub>2<\/jats:sub>(C:)<jats:sub>2<\/jats:sub>]Li(THF)<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub> (Ar=Ph, <jats:bold>13\u2009a<\/jats:bold>; 4\u2010Tol, <jats:bold>13\u2009b<\/jats:bold>; 4\u2010DMP, <jats:bold>13\u2009c<\/jats:bold>), which on treatment with Ph<jats:sub>2<\/jats:sub>PCl affords cationic vicinal bisphosphine derivatives [ArC{N(2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>)}<jats:sub>2<\/jats:sub>{C(PPh<jats:sub>2<\/jats:sub>}<jats:sub>2<\/jats:sub>]X (Ar=Ph, <jats:bold>14\u2009a<\/jats:bold>\u2010X, X=Br or I; 4\u2010Tol, <jats:bold>14\u2009b<\/jats:bold>\u2010Br; 4\u2010DMP, <jats:bold>14\u2009c<\/jats:bold>\u2010Br).<\/jats:p>","DOI":"10.1002\/chem.201800260","type":"journal-article","created":{"date-parts":[[2018,1,24]],"date-time":"2018-01-24T06:32:55Z","timestamp":1516775575000},"page":"3716-3720","source":"Crossref","is-referenced-by-count":44,"title":["The Viability of C5\u2010Protonated\u2010 and C4,C5\u2010Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4810-9203","authenticated-orcid":false,"given":"Dennis","family":"Rottsch\u00e4fer","sequence":"first","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Falk","family":"Ebeler","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Till","family":"Strothmann","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beate","family":"Neumann","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hans\u2010Georg","family":"Stammler","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas","family":"Mix","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2146-5432","authenticated-orcid":false,"given":"Rajendra S.","family":"Ghadwal","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Lehrstuhl f\u00fcr, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr, Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstr. 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,2,15]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature13384"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.CO;2-A"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703883"},{"key":"e_1_2_2_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703883"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar5003494"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic502231m"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc51174j"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300196u"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1221138"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702148"},{"key":"e_1_2_2_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702148"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00285"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6DT02158A"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00264"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702433"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703530"},{"key":"e_1_2_2_18_1","unstructured":"\u00a0"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2015.06.012"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802956"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802956"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/b902238b"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001865"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001865"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60146c"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/om400858y"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209109"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209109"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC00255F"},{"key":"e_1_2_2_28_1","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501841"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200501841"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC05289G"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703215"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600765"},{"key":"e_1_2_2_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600765"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000165"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000165"},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101130"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001864"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001864"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0423769"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2012.09.006"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH11265"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr8005087"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2006.08.006"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/b107881j"},{"key":"e_1_2_2_44_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1178206"},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507206"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507206"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402560"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja408589p"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja106631r"},{"key":"e_1_2_2_50_1","unstructured":"\u00a0"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2014.09.020"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2016.02.011"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7DT01199G"},{"key":"e_1_2_2_54_1","unstructured":"\u00a0"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7DT03099A"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405923"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/om900919f"},{"key":"e_1_2_2_58_1","unstructured":"One reviewer pointed out that proton exchange between4and some unreacted3\u2009a-X may also cause the broadening of1H\u2005NMR signals."},{"key":"e_1_2_2_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19951280307"},{"key":"e_1_2_2_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5DT01362C"},{"key":"e_1_2_2_61_1","unstructured":"See the Supporting Information for further details including synthesis analytical data spectroscopic details along with the plots of NMR and ESI spectra and details of X-ray diffraction analyses."},{"key":"e_1_2_2_62_1","unstructured":"CCDC1811072\u20131811079 contain the supplementary crystallographic data for compounds6 7 8-I 9-I 11 12 14\u2009a-I and14\u2009b-Br respectively. These data are provided free of charge byThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_2_63_1","unstructured":"\u00a0"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic201290g"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/b814486a"},{"key":"e_1_2_2_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409800"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409800"},{"key":"e_1_2_2_67_1","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7DT01778B"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.3390\/catal7090262"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00662"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.201600308"},{"key":"e_1_2_2_72_1","unstructured":"\u00a0"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201401073"},{"key":"e_1_2_2_73_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201401073"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402375"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201800260","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201800260","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:34:03Z","timestamp":1760279643000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201800260"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,2,15]]},"references-count":87,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2018,3,12]]}},"alternative-id":["10.1002\/chem.201800260"],"URL":"https:\/\/doi.org\/10.1002\/chem.201800260","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,2,15]]}}}