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Here, lead\u2010halide perovskite microcrystals are shown to mediate cross\u2010dehydrogenative C\u2500N coupling of aromatic heterocyclic amines in air at room temperature by controlling complementary radical species at semiconductor interfaces. Phenoxazine undergoes efficient oxidative dimerization, whereas closely related scaffolds such as phenothiazine and 9,9\u2010dimethyl\u20109,10\u2010dihydroacridine display markedly different reactivity profiles despite comparable oxidation potentials. Combined electrochemical, spectroscopic, and radical\u2010trapping experiments reveal that efficient C\u2500N bond formation correlates with the concurrent generation of radical cation and neutral aminyl species at the catalyst\u2013substrate interface. UV\u2013vis monitoring under controlled atmospheres establishes the necessity of oxygen for sustaining complementary radical populations, while spin\u2010unrestricted DFT calculations identify substrate\u2010dependent spin localization, as well as distinct N\u2500H activation barriers, as key factors of coupling efficiency. Interception of the photogenerated aminyl radicals enables hetero\u2010cross\u2010dehydrogenative coupling with naphthol and naphthylamine derivatives. These findings delineate mechanistic principles governing C\u2500N bond formation at semiconductor surfaces and position metal\u2010halide perovskites as tunable and recyclable platforms for N\u2010centered radical chemistry under mild conditions.<\/jats:p>","DOI":"10.1002\/smsc.70306","type":"journal-article","created":{"date-parts":[[2026,5,18]],"date-time":"2026-05-18T09:59:13Z","timestamp":1779098353000},"source":"Crossref","is-referenced-by-count":0,"title":["Intercepting Photogenerated Aminyl Radicals at Metal\u2010Halide Perovskite Microcrystals to Forge C\u2500N Bonds With Non\u2010Preactivated Substrates"],"prefix":"10.1002","volume":"6","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6969-2496","authenticated-orcid":false,"given":"Daniele","family":"Conelli","sequence":"first","affiliation":[{"name":"Dipartimento di Ingegneria Civile Ambientale del Territorio Edile e di Chimica (DICATECh) Politecnico di Bari  Bari 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