{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,5]],"date-time":"2026-11-05T16:21:51Z","timestamp":1793895711180,"version":"4.8.0"},"reference-count":69,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    A new, well\u2010defined, air\u2010stable\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocyclic carbene nickel(II) precatalyst [(IPr)Ni(\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methylphenethylamine)Cl] (IPr =\n                    <jats:italic>N,N\u2032\u2010<\/jats:italic>\n                    bis(2,6\u2010diisopropylphenyl)imidazol\u20102\u2010ylidene) was designed, synthesized, and evaluated for C\u2013N cross\u2010coupling reactions. This precatalyst is readily activated in the presence of base and efficiently promotes the amination of a variety of aryl chlorides with amines. Optimization studies established robust reaction conditions and revealed the influence of electronic and steric properties of the coupling partners on catalytic performance. The combination of operational simplicity, long\u2010term bench stability, and facile activation makes this NHC\u2013Ni precatalyst a good choice for nickel\u2010catalyzed C\u2013N bond formation.\n                  <\/jats:p>","DOI":"10.1002\/chem.71749","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T07:01:56Z","timestamp":1790665316000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["A Well\u2010Defined, Air\u2010Stable NHC\u2013Ni Precatalyst for C\u2013N Bond Formation"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-3721-506X","authenticated-orcid":false,"given":"Kianoosh","family":"Masoomi","sequence":"first","affiliation":[{"name":"Centre for Catalysis Research and Innovation (CCRI), Department of Chemistry and Biomolecular Sciences University of Ottawa  Ottawa Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00fcrgen","family":"Schulmeister","sequence":"additional","affiliation":[{"name":"Centre for Catalysis Research and Innovation (CCRI), Department of Chemistry and Biomolecular Sciences University of Ottawa  Ottawa Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-9221-0568","authenticated-orcid":false,"given":"Michael G.","family":"Organ","sequence":"additional","affiliation":[{"name":"Centre for Catalysis Research and Innovation (CCRI), Department of Chemistry and Biomolecular Sciences University of Ottawa  Ottawa Ontario Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,29]]},"reference":[{"key":"e_1_2_6_2_1","volume-title":"Catalytic Arylation Methods: From the Academic Lab to Industrial Processes","author":"Burke A. J.","year":"2015"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15082k"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/a908130e"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505268"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00512"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900587"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/0471212466"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619535"},{"key":"e_1_2_6_10_1","volume-title":"Organotransition Metal Chemistry: From Bonding to Catalysis","author":"Hartwig J. F.","year":"2010"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1983.927"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199513481"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00605-C"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201195"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar800098p"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106131"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00385"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.5b00302"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00072"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature13274"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02021"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002273"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100259t"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/op300236f"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0204933"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja207759e"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/0920-5861(90)85008-C"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/om0301637"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/om034067h"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja311940s"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aag0209"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201500305"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr950016l"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar990095d"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00054"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b04548"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b02919"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.3998\/ark.5550190.p008.915"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c01430"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5c03119"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-24094-9"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00001a054"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199721621"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature13384"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00067"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr940472u"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900074m"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01079-6"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/om0501879"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402022"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo070313d"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000223"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/om300566m"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b02187"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201800454"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms11073"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202100204"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC01253D"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503941"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo991699y"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00885"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0008486"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b01992"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03744"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202300494"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300485"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502822"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c04610"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol034264c"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2021.12.007"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71749","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71749","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71749","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T09:34:29Z","timestamp":1791970469000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71749"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,29]]},"references-count":69,"alternative-id":["10.1002\/chem.71749"],"URL":"https:\/\/doi.org\/10.1002\/chem.71749","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,29]]},"assertion":[{"value":"2026-08-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-18","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-29","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71749"}}