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While oxidative allylic C\u2500H amination using anilines has advanced significantly, achieving intermolecular reductive allylic C\u2500H amination of olefins with readily available nitroarenes remains a considerable challenge. Here, we demonstrate that replacing silanes with a combination of protons and electrons enables selective reductive allylic C\u2500H amination, avoiding the competing hydroamination pathway. The key to this transformation is the use of 2,2,2\u2010trifluoroethanol (TFE) as the solvent. This process complements previous oxidative allylic C\u2500H amination by eliminating the need for noble metal catalysts while tolerating oxidizable or nucleophilic functional groups. Notably, this method facilitates the functionalization of bioactive compounds, underscoring its potential in medicinal chemistry. Furthermore, by leveraging its reactivity with trisubstituted olefins, this approach, when combined with metal hydride atom transfer (MHAT) reactions, offers a unique strategy for regioselective and modular difunctionalization of aliphatic olefins. Experimental and computational mechanistic studies highlight the crucial roles of TFE in stabilizing the nitrosoarene intermediate and promoting the key nitroso\u2010ene step.<\/jats:p>","DOI":"10.1002\/anie.202504750","type":"journal-article","created":{"date-parts":[[2025,4,9]],"date-time":"2025-04-09T22:57:16Z","timestamp":1744239436000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Iron\u2010Catalyzed Reductive Allylic C\u2500H Amination of Olefin with Nitroarenes via Intermolecular Nitroso Ene Reaction"],"prefix":"10.1002","volume":"64","author":[{"given":"Shaolong","family":"Qi","sequence":"first","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangming Advanced Research Institute and Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 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