{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T20:06:25Z","timestamp":1784318785762,"version":"3.55.0"},"reference-count":111,"publisher":"Wiley","issue":"36","license":[{"start":{"date-parts":[[2023,5,8]],"date-time":"2023-05-08T00:00:00Z","timestamp":1683504000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22001230 and 22271251"],"award-info":[{"award-number":["22001230 and 22271251"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["226-2022-00224"],"award-info":[{"award-number":["226-2022-00224"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,6,27]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The incorporation of the privileged amino functionality is of paramount importance in organic synthesis. In contrast to the well\u2010developed amination methods for alkenes, the dearomative amination of arenes is largely underexplored due to the inherently inert reactivity of arene \u03c0\u2010bonds and selectivity challenges. Herein, we report an intermolecular dearomative aminofunctionalization via direct nucleophilic addition of simple amines to chromium\u2010bound arenes. This multicomponent 1,2\u2010amination\/carbonylation reaction enables rapid access to complicated alicyclic compounds containing amino and amide functionalities from benzene derivatives under CO\u2010gas\u2010free conditions, which also represents the first application of nitrogen\u2010based nucleophiles in \u03b7<jats:sup>6<\/jats:sup>\u2010coordination\u2010induced arene dearomatizations.<\/jats:p>","DOI":"10.1002\/chem.202300776","type":"journal-article","created":{"date-parts":[[2023,4,19]],"date-time":"2023-04-19T05:41:14Z","timestamp":1681882874000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Intermolecular Dearomative 1,2\u2010Amination\/Carbonylation via Nucleophilic Addition of Simple Amines to Arene \u03c0\u2010Bonds"],"prefix":"10.1002","volume":"29","author":[{"given":"Zheng\u2010Jian","family":"Li","sequence":"first","affiliation":[{"name":"Department of Chemistry Zhejiang University  310027 Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming\u2010Yang","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  310027 Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chu\u2010Qiao","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  310027 Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei\u2010Long","family":"Zeng","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  310027 Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8858-114X","authenticated-orcid":false,"given":"Wei","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Zhejiang University  310027 Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,5,8]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"For selected books see:"},{"key":"e_1_2_9_2_2","volume-title":"Amines: Synthesis, Properties and Applications","author":"Lawrence S. A.","year":"2004"},{"key":"e_1_2_9_3_2","volume-title":"Amino Group Chemistry: From Synthesis to the Life Sciences","author":"Ricci A.","year":"2008"},{"key":"e_1_2_9_4_1","unstructured":"For a book see:"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527613182"},{"key":"e_1_2_9_6_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21030352"},{"key":"e_1_2_9_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100371y"},{"key":"e_1_2_9_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs400138b"},{"key":"e_1_2_9_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA06633A"},{"key":"e_1_2_9_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101460"},{"key":"e_1_2_9_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101460"},{"key":"e_1_2_9_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00054D"},{"key":"e_1_2_9_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04767"},{"key":"e_1_2_9_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00400A"},{"key":"e_1_2_9_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306788"},{"key":"e_1_2_9_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300389u"},{"key":"e_1_2_9_16_1","unstructured":"For 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see:"},{"key":"e_1_2_9_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja7114426"},{"key":"e_1_2_9_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901484"},{"key":"e_1_2_9_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901484"},{"key":"e_1_2_9_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09939"},{"key":"e_1_2_9_26_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2386"},{"key":"e_1_2_9_27_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_9_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00692"},{"key":"e_1_2_9_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b01951"},{"key":"e_1_2_9_30_1","unstructured":"For selected reviews on arene dearomatizations see:"},{"key":"e_1_2_9_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527698479"},{"key":"e_1_2_9_32_2","volume-title":"Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds","author":"Mortier 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Chem."},{"key":"e_1_2_9_62_1","unstructured":"\u00a0"},{"key":"e_1_2_9_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.202100103"},{"key":"e_1_2_9_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c03529"},{"key":"e_1_2_9_65_1","unstructured":"For selected reviews of \u03b72-arene complexes see:"},{"key":"e_1_2_9_66_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(99)00249-0"},{"key":"e_1_2_9_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2004.03.013"},{"key":"e_1_2_9_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00480"},{"key":"e_1_2_9_69_1","unstructured":"For selected reviews of \u03b76-arene complexes see:"},{"key":"e_1_2_9_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902852"},{"key":"e_1_2_9_71_2","volume-title":"Topics in Organometallic Chemistry, Vol.\u20057","author":"K\u00fcndig E. P.","year":"2004"},{"key":"e_1_2_9_72_1","unstructured":"The toxicity of low valent chromium compounds is low see: the ORL-RAT LD50value (single oral dose for rats mg\/Kg) of (\u03b76-benzene)Cr(CO)3is 500.1\u2005mg\/Kg (Data source from Sigma-Aldrich MSDs:http:\/\/www.sigmaaldrich.cn\/CN\/en\/sds\/aldrich\/119318) which is slightly toxic according to the common description. For more references see:"},{"key":"e_1_2_9_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja409076z"},{"key":"e_1_2_9_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.7b00605"},{"key":"e_1_2_9_75_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0039-1690764"},{"key":"e_1_2_9_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.1c00096"},{"key":"e_1_2_9_77_1","unstructured":"For selected examples using (\u03b76-arene)Cr(CO)3reagents see:"},{"key":"e_1_2_9_78_2","doi-asserted-by":"publisher","DOI":"10.1039\/b606665h"},{"key":"e_1_2_9_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509917"},{"key":"e_1_2_9_79_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201509917"},{"key":"e_1_2_9_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409065"},{"key":"e_1_2_9_80_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409065"},{"key":"e_1_2_9_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja512271p"},{"key":"e_1_2_9_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711816"},{"key":"e_1_2_9_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711816"},{"key":"e_1_2_9_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04726"},{"key":"e_1_2_9_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b05334"},{"key":"e_1_2_9_85_1","unstructured":"\u00a0"},{"key":"e_1_2_9_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210312"},{"key":"e_1_2_9_86_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202210312"},{"key":"e_1_2_9_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202218961"},{"key":"e_1_2_9_87_3","volume":"135","year":"2022","journal-title":"Angew. Chem."},{"key":"e_1_2_9_88_1","unstructured":"For recent reviews on carbonylation see:"},{"key":"e_1_2_9_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300100s"},{"key":"e_1_2_9_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar400222k"},{"key":"e_1_2_9_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00068"},{"key":"e_1_2_9_92_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00615J"},{"key":"e_1_2_9_93_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2020.11.006"},{"key":"e_1_2_9_94_1","unstructured":"Deposition Number(s)2219539 (29)contain(s) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_9_95_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711816"},{"key":"e_1_2_9_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711816"},{"key":"e_1_2_9_96_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol100235b"},{"key":"e_1_2_9_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b13080"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202300776","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:18:03Z","timestamp":1760264283000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202300776"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,5,8]]},"references-count":111,"journal-issue":{"issue":"36","published-print":{"date-parts":[[2023,6,27]]}},"alternative-id":["10.1002\/chem.202300776"],"URL":"https:\/\/doi.org\/10.1002\/chem.202300776","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,5,8]]},"assertion":[{"value":"2023-03-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-05-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202300776"}}