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Herein we describe chiral iron complexes of <jats:italic>meso<\/jats:italic>\u2010 and <jats:italic>\u03b2<\/jats:italic>\u2010substituted\u2010porphyrins that can catalyze asymmetric intramolecular C(sp<jats:sup>3<\/jats:sup>)\u2212H amination of aryl and arylsulfonyl azides to afford chiral indolines (29 examples) and benzofused cyclic sulfonamides (17 examples), respectively, with up to 93\u2009% <jats:italic>ee<\/jats:italic> (yield: up to 99\u2009%) using 410\u2005nm light under mild conditions. Mechanistic studies, including DFT calculations, for the reactions of arylsulfonyl azides reveal that the Fe(NSO<jats:sub>2<\/jats:sub>Ar) intermediate generated in situ under photochemical conditions reacts with the C(sp<jats:sup>3<\/jats:sup>)\u2212H bond through a stepwise hydrogen atom transfer\/radical rebound mechanism, with enantioselectivity arising from cooperative noncovalent interactions between the Fe(NSO<jats:sub>2<\/jats:sub>Ar) unit and the peripheral substituents of the chiral porphyrin scaffold.<\/jats:p>","DOI":"10.1002\/anie.202218577","type":"journal-article","created":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T17:30:22Z","timestamp":1675099822000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Chiral Iron Porphyrins Catalyze Enantioselective Intramolecular C(sp<sup>3<\/sup>)\u2212H Bond Amination Upon Visible\u2010Light Irradiation"],"prefix":"10.1002","volume":"62","author":[{"given":"Hua\u2010Hua","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Chemistry Southern University of Science and Technology  Shenzhen Guangdong 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hui","family":"Shao","sequence":"additional","affiliation":[{"name":"Department of Chemistry Southern University of Science and Technology  Shenzhen Guangdong 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guanglong","family":"Huang","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University, and Chemistry and Chemical Engineering Guangdong Laboratory  Guangdong 515063 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