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The study showcased that while \u03b1\u2010aryl\u2010\u03b1\u2010chlorohydroxamate could be activated by a combination of base and 1,1,1,3,3,3\u2010hexafluoro\u20102\u2010propanol (HFIP) into the corresponding azaoxyallyl cations, it could further emerge into a \u03c0\u2010extended species involving the adjacent \u03b1\u2010aryl moiety, and this transition is contingent on electronic effects of the aromatic ring as well as on \u03b1\u2010substituents. An effective activation of the \u03b1\u2010aromatic ring could pave the path for intramolecular Ar(C<jats:italic>sp<\/jats:italic><jats:sup>2<\/jats:sup>)\u2010N bond formation towards oxindoles. Control experiments and DFT calculations suggested that a non\u2010pericyclic nucleophilic amination pathway is most likely operative and precluded the possibility of concerted or electrophilic amination mechanism. HFIP as the reaction solvent plays pivotal roles in the transformation.<\/jats:p>","DOI":"10.1002\/chem.202201208","type":"journal-article","created":{"date-parts":[[2022,8,9]],"date-time":"2022-08-09T12:32:16Z","timestamp":1660048336000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Experimental and Theoretical Investigation of an Azaoxyallyl Cation\u2010Templated Intramolecular Aryl Amination Leading to Oxindole Derivatives"],"prefix":"10.1002","volume":"28","author":[{"given":"Tishyasoumya","family":"Bera","sequence":"first","affiliation":[{"name":"Department of Biological and Synthetic Chemistry Centre of Biomedical Research (CBMR)  SGPGIMS Campus. 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Lett."},{"key":"e_1_2_8_25_2","first-page":"10","author":"Lei X.","year":"2022","journal-title":"Org. Lett."},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01933"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02269"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02621"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC02378D"},{"key":"e_1_2_8_30_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/open.201900220"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB01683J"},{"key":"e_1_2_8_33_1","doi-asserted-by":"crossref","unstructured":"Structure and reaction conditions govern the formation of transient or isolable \u03b1-lactams. V. Cesare T.\u2005M. Lyons I. Lengyal Synthesis2002 12 1716. 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These reactions did not give any oxindole product under the reaction condition (cf. Ref.\u2005[8d]). On the other hand for example 41could be directly achieved from corresponding \u03b1-hydroxyhydroxamate in presence of SOCl2in DCM albeit this was a very slow reaction (ca. 50\u2009% conversion in 12h\u2009 This particular reaction afforded high yield in short reaction time (2) when SOCl2and Na2CO3were used in HFIP. While MS analysis indicated the presence of \u03b1-chlorohydroxamate in reaction mixture improved reaction efficiency in HFIP can be corroborated to in situ formation of azaoxyallyl cation species (either from \u03b1-chloro or \u03b1-OSOCl system)."},{"key":"e_1_2_8_76_1","unstructured":"See section 6.1 in the Supporting Information for influence of various groups attached to the nitrogen of \u03b1-haloamide. The N\u2212O-alkyl group which is known to impart crucial roles for generating azaoxyallyl cation species only worked suitably in the current study."},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol302743k"},{"key":"e_1_2_8_78_1","unstructured":"For selected relevant examples on metal catalysed intramolecular electrophilic amination leading to various N-heterocycles see:"},{"key":"e_1_2_8_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00331a053"},{"key":"e_1_2_8_80_2","first-page":"353","author":"Paudyal M. P.","year":"2016","journal-title":"Science."},{"key":"e_1_2_8_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b02939"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b05476"},{"key":"e_1_2_8_83_2","first-page":"5996","volume":"13","author":"Hwan S","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_8_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1067993"},{"key":"e_1_2_8_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo901224k"},{"key":"e_1_2_8_86_1","unstructured":"For selected examples on Metal-free intramolecular aromatic amination processes see:"},{"key":"e_1_2_8_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00071a019"},{"key":"e_1_2_8_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058026j"},{"key":"e_1_2_8_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503671"},{"key":"e_1_2_8_89_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503671"},{"key":"e_1_2_8_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705916"},{"key":"e_1_2_8_90_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201705916"},{"key":"e_1_2_8_91_2","first-page":"54","author":"Kawase M.","year":"1989","journal-title":"J. Org. Chem."},{"key":"e_1_2_8_92_2","first-page":"68","author":"Creary X.","year":"2003","journal-title":"J. Org. Chem."},{"key":"e_1_2_8_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07830"},{"key":"e_1_2_8_94_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2725(08)60002-1"},{"key":"e_1_2_8_95_1","doi-asserted-by":"crossref","unstructured":"Localization of positive charge on nitrogen of N-OMe moiety in \u03b1-halo oximether system is precedented which followed a SEAr annulation through adjacent arene ring; see X. Creary E.\u2005A. Burtch Z. Jiang J. Org. Chem.2003 68 1117.","DOI":"10.1021\/jo026468x"},{"key":"e_1_2_8_96_1","unstructured":"We also tested the same \u03b1-chloro-\u03b1 \u03b1-diphenylamide as showcased in Scheme\u20051c under our developed conditions but it was unreactive."},{"key":"e_1_2_8_97_1","unstructured":"For reviews on Nazarov and Nazarov-type cyclizations see"},{"key":"e_1_2_8_98_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB00804A"},{"key":"e_1_2_8_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300134"},{"key":"e_1_2_8_100_1","unstructured":"For relevant examples on imino-Nazarov processes see:Nummerierung?"},{"key":"e_1_2_8_101_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC08783F"},{"key":"e_1_2_8_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo202477h"},{"key":"e_1_2_8_103_2","doi-asserted-by":"publisher","DOI":"10.1039\/b927564a"},{"key":"e_1_2_8_104_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201805641"},{"key":"e_1_2_8_104_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201805641"},{"key":"e_1_2_8_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4012663"},{"key":"e_1_2_8_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405251"},{"key":"e_1_2_8_106_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405251"},{"key":"e_1_2_8_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02441"},{"key":"e_1_2_8_108_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603592"},{"key":"e_1_2_8_109_1","unstructured":"\u00a0"},{"key":"e_1_2_8_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00287a004"},{"key":"e_1_2_8_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00257a009"},{"key":"e_1_2_8_112_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03103"},{"key":"e_1_2_8_113_1","unstructured":"\u00a0"},{"key":"e_1_2_8_114_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960582d"},{"key":"e_1_2_8_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030088"},{"key":"e_1_2_8_116_1","unstructured":"\u00a0"},{"key":"e_1_2_8_117_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400037"},{"key":"e_1_2_8_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo900270e"},{"key":"e_1_2_8_119_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001162"},{"key":"e_1_2_8_120_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527211797636165"},{"key":"e_1_2_8_121_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900103"},{"key":"e_1_2_8_122_2","first-page":"6021","author":"Narayan R.","year":"2021","journal-title":"Eur. 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