{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T21:07:48Z","timestamp":1788556068462,"version":"build-2803163510"},"reference-count":96,"publisher":"Wiley","issue":"48","license":[{"start":{"date-parts":[[2013,10,14]],"date-time":"2013-10-14T00:00:00Z","timestamp":1381708800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2013,11,25]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The <jats:italic>meta<\/jats:italic>\u2010terphenyl diphosphine, <jats:italic>m<\/jats:italic>\u2010P<jats:sub>2<\/jats:sub>, <jats:bold>1<\/jats:bold>, was utilized to support Ni centers in the oxidation states 0, I, and II. A series of complexes bearing different substituents or ligands at Ni was prepared to investigate the dependence of metal\u2013arene interactions on oxidation state and substitution at the metal center. Complex (<jats:italic>m<\/jats:italic>\u2010P<jats:sub>2<\/jats:sub>)Ni (<jats:bold>2<\/jats:bold>) shows strong Ni<jats:sup>0<\/jats:sup>\u2013arene interactions involving the central arene ring of the terphenyl ligand both in solution and the solid state. These interactions are significantly less pronounced in Ni<jats:sup>0<\/jats:sup> complexes bearing L\u2010type ligands (<jats:bold>2\u2010L<\/jats:bold>: L=CH<jats:sub>3<\/jats:sub>CN, CO, Ph<jats:sub>2<\/jats:sub>CN<jats:sub>2<\/jats:sub>), Ni<jats:sup>I<\/jats:sup>X complexes (<jats:bold>3\u2010X<\/jats:bold>: X=Cl, BF<jats:sub>4<\/jats:sub>, N<jats:sub>3<\/jats:sub>, N<jats:sub>3<\/jats:sub>B(C<jats:sub>6<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>), and [(<jats:italic>m<\/jats:italic>\u2010P<jats:sub>2<\/jats:sub>)Ni<jats:sup>II<\/jats:sup>Cl<jats:sub>2<\/jats:sub>] (<jats:bold>4<\/jats:bold>). Complex <jats:bold>2<\/jats:bold> reacts with substrates, such as diphenyldiazoalkane, sulfur ylides (Ph<jats:sub>2<\/jats:sub>S\uf8feCH<jats:sub>2<\/jats:sub>), organoazides (RN<jats:sub>3<\/jats:sub>: R=<jats:italic>para<\/jats:italic>\u2010C<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>OMe, <jats:italic>para<\/jats:italic>\u2010C<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>CF<jats:sub>3<\/jats:sub>, 1\u2010adamantyl), and N<jats:sub>2<\/jats:sub>O with the locus of observed reactivity dependent on the nature of the substrate. These reactions led to isolation of an \u03b7<jats:sup>1<\/jats:sup>\u2010diphenyldiazoalkane adduct (<jats:bold>2\u2010Ph<jats:sub>2<\/jats:sub>CN<jats:sub>2<\/jats:sub><\/jats:bold>), methylidene insertion into a Ni\uf8ffP bond followed by rearrangement of a nickel\u2010bound phosphorus ylide (<jats:bold>5<\/jats:bold>) to a benzylphosphine (<jats:bold>6)<\/jats:bold>, Staudinger oxidation of the phosphine arms, and metal\u2010mediated nitrene insertion into an arene C\uf8ffH bond of <jats:bold>1<\/jats:bold>, all derived from the same compound (<jats:bold>2<\/jats:bold>). Hydrogen\u2010atom abstraction from a Ni<jats:sup>I<\/jats:sup>\u2013amide (<jats:bold>9<\/jats:bold>) and the resulting nitrene transfer supports the viability of Ni\u2013imide intermediates in the reaction of <jats:bold>1<\/jats:bold> with 1\u2010azido\u2010arenes.<\/jats:p>","DOI":"10.1002\/chem.201302539","type":"journal-article","created":{"date-parts":[[2013,10,14]],"date-time":"2013-10-14T08:46:45Z","timestamp":1381740405000},"page":"16453-16460","source":"Crossref","is-referenced-by-count":47,"title":["Arene C\uf8ffH Amination at Nickel in Terphenyl\u2013Diphosphine Complexes with Labile Metal\u2013Arene Interactions"],"prefix":"10.1002","volume":"19","author":[{"given":"David E.","family":"Herbert","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nadia C.","family":"Lara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Theodor","family":"Agapie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,10,14]]},"reference":[{"key":"e_1_2_5_1_2","unstructured":"\u00a0"},{"key":"e_1_2_5_2_2","volume-title":"Metal\u2013Ligand Multiple Bonds","author":"Nugent W. A.","year":"1988"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(03)00048-1"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1080\/02603590902768875"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2011.01.009"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B006015L"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020043t"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500554"},{"key":"e_1_2_5_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500554"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2005.1304"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature06485"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/b905820f"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c005219c"},{"key":"e_1_2_5_13_2","first-page":"3954","author":"Barker T. J.","year":"2011","journal-title":"Synthesis"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-90-481-3698-8_6"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/om300840z"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar200318q"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2dt32063k"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol303167n"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0381914"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/b820620a"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja904370h"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic900219b"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja110066j"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1233701"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102028"},{"key":"e_1_2_5_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102028"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja203434c"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja204800a"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/om3009102"},{"key":"e_1_2_5_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2090965"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1101213"},{"key":"e_1_2_5_31_2","unstructured":"\u00a0"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00345a071"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja953659r"},{"key":"e_1_2_5_34_2","unstructured":"\u00a0"},{"key":"e_1_2_5_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001147t"},{"key":"e_1_2_5_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028448i"},{"key":"e_1_2_5_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja057165y"},{"key":"e_1_2_5_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2005303"},{"key":"e_1_2_5_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2010.11.031"},{"key":"e_1_2_5_40_2","unstructured":"\u00a0"},{"key":"e_1_2_5_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja026852b"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja036308i"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462529"},{"key":"e_1_2_5_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462529"},{"key":"e_1_2_5_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107288x"},{"key":"e_1_2_5_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307699u"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/b204846a"},{"key":"e_1_2_5_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0533186"},{"key":"e_1_2_5_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja302149k"},{"key":"e_1_2_5_49_2","unstructured":"\u00a0"},{"key":"e_1_2_5_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804304"},{"key":"e_1_2_5_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804304"},{"key":"e_1_2_5_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307229e"},{"key":"e_1_2_5_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja306674h"},{"key":"e_1_2_5_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010358a"},{"key":"e_1_2_5_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja805530z"},{"key":"e_1_2_5_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0269183"},{"key":"e_1_2_5_56_2","unstructured":"For intramolecular aromatic amination through iron\u2010mediated nitrene insertion see:"},{"key":"e_1_2_5_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351605"},{"key":"e_1_2_5_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351605"},{"key":"e_1_2_5_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0724137"},{"key":"e_1_2_5_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307279r"},{"key":"e_1_2_5_60_2","unstructured":"\u00a0"},{"key":"e_1_2_5_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101699a"},{"key":"e_1_2_5_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja200368y"},{"key":"e_1_2_5_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja300326t"},{"key":"e_1_2_5_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102797"},{"key":"e_1_2_5_64_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102797"},{"key":"e_1_2_5_65_2","unstructured":"\u00a0"},{"key":"e_1_2_5_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/om960389s"},{"key":"e_1_2_5_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075630g"},{"key":"e_1_2_5_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900290"},{"key":"e_1_2_5_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900290"},{"key":"e_1_2_5_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/om1008499"},{"key":"e_1_2_5_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/om100001m"},{"key":"e_1_2_5_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2DT32008H"},{"key":"e_1_2_5_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050781"},{"key":"e_1_2_5_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/JR9280003193"},{"key":"e_1_2_5_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39840001217"},{"key":"e_1_2_5_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.197200035"},{"key":"e_1_2_5_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39740000761"},{"key":"e_1_2_5_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic801035z"},{"key":"e_1_2_5_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja211603f"},{"key":"e_1_2_5_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic7023764"},{"key":"e_1_2_5_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic8024205"},{"key":"e_1_2_5_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028267g"},{"key":"e_1_2_5_82_2","unstructured":"\u00a0"},{"key":"e_1_2_5_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00234a044"},{"key":"e_1_2_5_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00234a043"},{"key":"e_1_2_5_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00033a049"},{"key":"e_1_2_5_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017787t"},{"key":"e_1_2_5_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja107115q"},{"key":"e_1_2_5_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047052z"},{"key":"e_1_2_5_89_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2006.08.054"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201302539","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201302539","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:37:34Z","timestamp":1760301454000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201302539"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,10,14]]},"references-count":96,"journal-issue":{"issue":"48","published-print":{"date-parts":[[2013,11,25]]}},"alternative-id":["10.1002\/chem.201302539"],"URL":"https:\/\/doi.org\/10.1002\/chem.201302539","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,10,14]]}}}