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While on\u2010surface synthesis has demonstrated efficient coupling strategies for  systems, \u2500 bond formation on surfaces remains largely unexplored. Here, we report the on\u2010surface analogue of Friedel\u2013Crafts alkylation on a metal surface: an intramolecular \u2500 coupling reaction based on a specifically designed fluorinated aromatic reactant, with the metal surface itself acting as catalyst. Our reactant\u2010catalyst design stabilizes the key intermediate; allowing for direct real\u2010space imaging at the single\u2010molecule level. By integrating high\u2010resolution scanning tunneling microscopy, x\u2010ray photoelectron spectroscopy, and first\u2010principles computations, we elucidate each elementary step of the on\u2010surface Friedel\u2013Crafts alkylation pathway. These results open a new route toward the controlled integration of  centers into hybrid \u2500 carbon nanostructures, expanding the synthetic toolbox of on\u2010surface chemistry.<\/jats:p>","DOI":"10.1002\/anie.3848864","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T03:35:40Z","timestamp":1790739340000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["On\u2010Surface Friedel\u2013Crafts Alkylation Through a Stabilized Intermediate Complex"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4407-5931","authenticated-orcid":false,"given":"Paul","family":"Schweer","sequence":"first","affiliation":[{"name":"Physikalische Chemie I Ruhr\u2010Universit\u00e4t Bochum Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christoph J.","family":"Vonnemann","sequence":"additional","affiliation":[{"name":"Organische Chemie II Ruhr\u2010Universit\u00e4t Bochum Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nishanth","family":"Arumugam","sequence":"additional","affiliation":[{"name":"Department of Chemistry Hofstra University New York USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4125-159X","authenticated-orcid":false,"given":"Stefan M.","family":"Huber","sequence":"additional","affiliation":[{"name":"Organische Chemie II Ruhr\u2010Universit\u00e4t Bochum Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1507-2667","authenticated-orcid":false,"given":"Daniel P.","family":"Miller","sequence":"additional","affiliation":[{"name":"Department of Chemistry Hofstra University New York 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