{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T22:41:23Z","timestamp":1781736083372,"version":"3.54.5"},"reference-count":95,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2022,11,27]],"date-time":"2022-11-27T00:00:00Z","timestamp":1669507200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["KN 240\/19-2"],"award-info":[{"award-number":["KN 240\/19-2"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","award":["57507438"],"award-info":[{"award-number":["57507438"]}],"id":[{"id":"10.13039\/501100001655","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":[[2023,1,27]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We describe an iron\u2010catalyzed asymmetric oxidative C\u2212C coupling of diarylamines which proceeds at room temperature with air as final oxidant. Using hexadecafluorophthalocyanine\u2010iron(II) as catalyst in the presence of catalytic amounts of an axially chiral biaryl phosphoric acid, the resulting chiral 2,2\u2032\u2010diamino\u20101,1\u2032\u2010biaryls are obtained in up to 90\u2009% <jats:italic>ee<\/jats:italic> as confirmed by chiral HPLC. A detailed mechanism has been proposed with a radical cation\u2010chiral phosphate ion pair as key intermediate leading to the observed asymmetric induction.<\/jats:p>","DOI":"10.1002\/chem.202203269","type":"journal-article","created":{"date-parts":[[2022,10,21]],"date-time":"2022-10-21T12:14:20Z","timestamp":1666354460000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Atroposelective Synthesis of 2,2\u2032\u2010Bis(arylamino)\u20101,1\u2032\u2010biaryls by Oxidative Iron(III)\u2010 and Phosphoric Acid\u2010Catalyzed C\u2212C Coupling of Diarylamines**"],"prefix":"10.1002","volume":"29","author":[{"given":"Raphael F.","family":"Fritsche","sequence":"first","affiliation":[{"name":"Fakult\u00e4t Chemie Technische Universit\u00e4t Dresden  Bergstra\u00dfe 66 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tristan","family":"Schuh","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Chemie Technische Universit\u00e4t Dresden  Bergstra\u00dfe 66 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga","family":"Kataeva","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Chemie Technische Universit\u00e4t Dresden  Bergstra\u00dfe 66 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9631-5239","authenticated-orcid":false,"given":"Hans\u2010Joachim","family":"Kn\u00f6lker","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Chemie Technische Universit\u00e4t Dresden  Bergstra\u00dfe 66 01069 Dresden Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,11,27]]},"reference":[{"key":"e_1_2_7_1_1","first-page":"1","volume-title":"Prog. Chem. Org. Nat. Prod.","author":"Bringmann G.","year":"2001"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100155e"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901719"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901719"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201000485"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2017.11.050"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0747573"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar200048d"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b01860"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr5001496"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00197"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00178a005"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/0926-860X(95)00097-6"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr040652w"},{"key":"e_1_2_7_13_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462661"},{"key":"e_1_2_7_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462661"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b608470m"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800378"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b821092f"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00012B"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378712"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500869"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB01304K"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01306"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20843"},{"key":"e_1_2_7_24_1","unstructured":"\u00a0"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol015595x"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804570b"},{"key":"e_1_2_7_27_1","unstructured":"\u00a0"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol015505o"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02552"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01734"},{"key":"e_1_2_7_31_1","unstructured":"\u00a0"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500425u"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.6b00272"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00772"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00688B"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901391u"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja105442m"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11198"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC07834G"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25040852"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c13020"},{"key":"e_1_2_7_43_1","unstructured":"\u00a0"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00087a036"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202058r"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.01.075"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612613"},{"key":"e_1_2_7_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612613"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/celc.201800422"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00032a055"},{"key":"e_1_2_7_50_1","unstructured":"\u00a0"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja401709k"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304039"},{"key":"e_1_2_7_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304039"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-019-0247-1"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50079a045"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201610168"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201610168"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201704554"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25071608"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905595"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202104292"},{"key":"e_1_2_7_60_1","unstructured":"\u00a0"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9807565"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016017e"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800485s"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802861s"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja506133z"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC02494J"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702107"},{"key":"e_1_2_7_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702107"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02849"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900206p"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja076498n"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00512"},{"key":"e_1_2_7_72_1","unstructured":"Crystallization ofrac-3\u2009afrom isohexane\/dichloromethane afforded single crystals suitable for X-ray analysis.Crystallographic data forrac-3\u2009a: C32H24N2 M=436.53\u2005g\u2009mol\u22121 crystal size: 0.214\u00d70.282\u00d70.451\u2005mm monoclinic space groupC2\/c a=11.1267(3) b=14.4065(5) c=14.5799(5) \u00c5 \u03b2=91.4970(10)\u00b0 V=2336.31(13) \u00c53 Z=4 \u03c1calcd=1.241\u2005g\u2009cm\u22123 \u03bc=0.072\u2005mm\u22121 \u03bb=0.71073\u2005\u00c5 T=150(2) K \u03b8range: 2.73-30.20\u00b0 reflections collected: 33287 independent: 3462 (Rint=0.0282) 158 parameters. The structure was solved by direct methods and refined by full-matrix least-squares onF2; finalRindices [I>2\u03c3(I)]:R1=0.0461 andwR2=0.1296; maximal residual electron density 0.378\u2005e\u2009\u00c5\u22123. Deposition Number(s)2204892contain(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_7_73_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC05240B"},{"key":"e_1_2_7_74_1","unstructured":"\u00a0"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1099-4831(07)00001-6"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1007\/128_2011_192"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200447s"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12827"},{"key":"e_1_2_7_79_1","unstructured":"\u00a0"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10165"},{"key":"e_1_2_7_81_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00806B"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.03.052"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13616"},{"key":"e_1_2_7_84_1","unstructured":"\u00a0"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00316a063"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b10152"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710537"},{"key":"e_1_2_7_87_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201710537"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203269","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202203269","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203269","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:42:28Z","timestamp":1760301748000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202203269"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,27]]},"references-count":95,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2023,1,27]]}},"alternative-id":["10.1002\/chem.202203269"],"URL":"https:\/\/doi.org\/10.1002\/chem.202203269","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,27]]},"assertion":[{"value":"2022-10-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-11-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202203269"}}