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To\u2010date, indole oxidation is limited to heme enzymes and synthetic iron porphyrin compounds. Herein, we demonstrate its efficient execution in a nonheme iron system. We report the oxidation of a broad range of indole substrates by a mononuclear nonheme iron(III)\u2010peroxo complex, [Fe\n                    <jats:sup>III<\/jats:sup>\n                    (O\n                    <jats:sub>2<\/jats:sub>\n                    )(12\u2010TMC)]\n                    <jats:sup>+<\/jats:sup>\n                    (\n                    <jats:bold>1<\/jats:bold>\n                    ), to their corresponding dioxygenated products. A significant kinetic isotope effect of 5.2 is determined in the reactions of\n                    <jats:bold>1<\/jats:bold>\n                    with\n                    <jats:italic>N\u2500<\/jats:italic>\n                    H and\n                    <jats:italic>N\u2013<\/jats:italic>\n                    D 2,3\u2010dimethylindoles, thereby supporting an\n                    <jats:italic>N\u2500<\/jats:italic>\n                    H hydrogen atom abstraction (HAT) mechanism. Interestingly, an alternative mechanism involving electrophilic addition of the iron\u2010peroxo group to the C2\u2013C3 double bond of the indole ring to form iron\u2010cycloadduct products predominates when\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methylated indoles are used as substrates. Theory supports the observed bifurcation reaction pathways, such as the\n                    <jats:italic>N\u2500<\/jats:italic>\n                    H HAT and the C2\u2013C3 double bond addition. Whether such bifurcation pathways have any role in determining the selectivity of biological indole oxidation reactions by heme\u2010dependent dioxygenases is now an inherent question, which should be investigated in future studies.\n                  <\/jats:p>","DOI":"10.1002\/anie.1874384","type":"journal-article","created":{"date-parts":[[2026,8,27]],"date-time":"2026-08-27T17:21:20Z","timestamp":1787851280000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Janus Reactivity of a Mononuclear Non\u2010Heme Iron(III)\u2010Peroxo Complex Toward Indole Oxidation"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4316-370X","authenticated-orcid":false,"given":"Wenjuan","family":"Zhu","sequence":"first","affiliation":[{"name":"Department of Chemistry and Nano Science Ewha Womans University  Seoul South Korea"},{"name":"Institut f\u00fcr Chemie Humboldt\u2010Universit\u00e4t Zu Berlin  Berlin German"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-5472-5847","authenticated-orcid":false,"given":"Peng","family":"Wu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of High\u2010Efficiency Utilization of Coal and Green Chemical Engineering School of Chemistry and Chemical Engineering Ningxia University  Yinchuan P. 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