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This method grants access to a range of functionalised hydrocarbons in excellent yields and can be upgraded to catalytic regimes when using <jats:italic>trans<\/jats:italic>\u2010stilbene, a 10\u2005mol% of the alkyl sodium base and toluene as a solvent. Extending this approach to aromatic ketones leads to the formation of stilbenes under mild reaction conditions, resulting from the deprotonative coupling of toluenes with ketones. Combining spectroscopic studies with the trapping and characterisation of key reaction intermediates, mechanistic insights have been gained, advancing the understanding of coordination effects in organosodium chemistry, and shedding light on their special reactivity profiles.<\/jats:p>","DOI":"10.1002\/chem.202400492","type":"journal-article","created":{"date-parts":[[2024,4,23]],"date-time":"2024-04-23T08:24:36Z","timestamp":1713860676000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Dual Basicity and Nucleophilicity of Organosodium Reagents in Benzylic C\u2212H Additions of Toluenes to Diarylethenes and Ketones"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3868-8571","authenticated-orcid":false,"given":"David E.","family":"Anderson","sequence":"first","affiliation":[{"name":"Departement f\u00fcr Chemie, Biochemie und Pharmazie Universit\u00e4t Bern  Freiestrasse 3 3012 Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alex H. 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