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It would significantly advance carbene chemistry if organic catalysts enable achieving classical metal\u2010carbene approaches otherwise unrealizable reactions. Herein, we report that chalcogen bonding catalysis can solve reactivity problem to achieve an elusive Buchner ring expansion of aryl ketones appending a cyclopropene moiety as carbene precursor. In this work, the ring\u2010opening of cyclopropene and the ring\u2010expansion of aryl systems were added in the field of noncovalent catalysis. This work demonstrates that chalcogen bonding can mediate carbene transformations beyond the known ionic approach. In contrast, transition metals such as rhodium, palladium, and copper complexes, could not solve the reactivity problem to achieve ring expansion of aryl ketones but instead these metal\u2010carbene approaches prefer the formation of furan side product. In addition, a thermal approach even being conducted at 200\u2009\u00b0C could not achieve this ring expansion reaction. Mechanistic investigation suggests Se\u22c5\u22c5\u22c5\u03c0 interaction with cyclopropene facilitates the ring\u2010opening of cyclopropene and chalcogen bonding with carbene intermediate changes the reaction pathway, thus overriding the furan reaction pathway.<\/jats:p>","DOI":"10.1002\/anie.202423746","type":"journal-article","created":{"date-parts":[[2024,12,23]],"date-time":"2024-12-23T15:49:32Z","timestamp":1734968972000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Chalcogen Bonding Catalysis Enables Ring\u2010Opening of Cyclopropene and Ring Expansion of Aryl Ketones"],"prefix":"10.1002","volume":"64","author":[{"given":"Haofu","family":"Zhu","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education Shandong University  Jinan 250100 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaomei","family":"Yang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education Shandong University  Jinan 250100 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education Shandong University  Jinan 250100 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hang","family":"Zhou","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry of the Ministry of Education Shandong University  Jinan 250100 P. R. 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