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Under iron\u2010catalyzed conditions, the carboxyamidation products were generated in high yield from both <jats:italic>Z<\/jats:italic>\u2010alkene and arene\u2010tethered substrates. DFT calculations indicate that the iron\u2010catalyzed carboxyamidation proceeds via a stepwise mechanism involving iron\u2010imidyl radical cyclization followed by intramolecular acyloxy transfer from the iron center to the alkenyl radical center to furnish the <jats:italic>cis<\/jats:italic>\u2010carboxyamidation product. Upon treatment with 4\u2010(dimethylamino)pyridine, the <jats:italic>Z<\/jats:italic>\u2010alkene\u2010tethered carboxyamidation products underwent selective O\u2192O acyl migration to generate 2\u2010acyloxy\u20105\u2010acyl pyrroles. Thermal O\u2192N acyl migration occurs during carboxyamidation if the <jats:italic>Z<\/jats:italic>\u2010alkene linker contains an alkyl or an aryl substituent at the \u03b2\u2010position of the carbonyl group. On the other hand, the arene linker\u2010containing compounds selectively undergo O\u2192N acyl migration to generate <jats:italic>N<\/jats:italic>\u2010acyl\u20103\u2010acylisoindolinones, and the corresponding O\u2192O acyl migration forming isoindole derivatives was not observed.<\/jats:p>","DOI":"10.1002\/chem.202303428","type":"journal-article","created":{"date-parts":[[2023,12,5]],"date-time":"2023-12-05T04:55:26Z","timestamp":1701752126000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Intramolecular Carboxyamidation of Alkyne\u2010Tethered <i>O<\/i>\u2010Acylhydroxamates through Formation of Fe(III)\u2010Nitrenoids"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-4488-5151","authenticated-orcid":false,"given":"Siyuan","family":"Su","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Illinois Chicago  845\u2005W. 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However the one-pot reaction is often 10\u201340\u2009% less in yields. See section 2.4 in Supporting Information for the one-pot protocol."},{"key":"e_1_2_9_92_1","unstructured":"Reviews on A1 3-strain:"},{"key":"e_1_2_9_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60254a001"},{"key":"e_1_2_9_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00098a009"},{"key":"e_1_2_9_95_1","unstructured":"\u00a0"},{"key":"e_1_2_9_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01046a062"},{"key":"e_1_2_9_97_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35093a"},{"key":"e_1_2_9_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.0c09549"},{"key":"e_1_2_9_99_1","unstructured":"Here we computationally considered the pathway initiated with an Fe(III) precatalyst leading to an Fe(IV) intermediate8. Under conditions catalyzed by Fe(II) species an Fe(III) nitreniod may be formed instead. 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