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Herein, we report a highly efficient and versatile dual photoredox system, involving a nickel aminopyridine coordination complex and a photocatalyst, for the cyclopropanation of aromatic olefins using dichloromethane, under visible\u2010light irradiation. The cyclopropanation protocol has been successfully applied at gram scale. Mechanistic studies suggest a Ni(II) pyridyl radical complex as the key intermediate for the homolytic cleavage of the C<jats:sub>sp3<\/jats:sub>\u2212Cl bond, generating a chloromethyl radical that is captured by the olefin coupling partner. Our findings also highlight the versatility of this methodology. By directing the radical\/polar crossover process, we were able to selectively drive the reaction towards either the formation of cyclopropyl derivatives or the corresponding non\u2010cyclic alkyl chloride products. The methodology also successfully apply to geminal dichloroalkanes, including the formation of spiro[2,2] compounds. Moreover, our methodology extends to the synthesis of deuterium\u2010labelled cyclopropanes, demonstrating its utility in isotopic labelling and broadening its applicability in chemical synthesis and drug development.<\/jats:p>","DOI":"10.1002\/anie.202405580","type":"journal-article","created":{"date-parts":[[2024,6,11]],"date-time":"2024-06-11T02:00:04Z","timestamp":1718071204000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Dichloromethane as C<sub>1<\/sub> Synthon for the Photoredox Catalytic Cyclopropanation of Aromatic Olefins"],"prefix":"10.1002","volume":"63","author":[{"given":"Jordi","family":"Arag\u00f3n","sequence":"first","affiliation":[{"name":"Institut Catal\u00e0 d'Investigaci\u00f3 Qu\u00edmica (ICIQ) Barcelona Institute of Science and Technology (BIST)  Av. 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