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Herein, we report the first divergent allene cyclopropanation with fluoroalkyl carbenes derived from fluoroalkyl triftosylhydrazones under distinct catalyst systems. The protocol achieves formal regiodivergent cyclopropanation of allenes at either terminal or internal double bonds; cyclopropanation of allenes with difluoromethyl or trifluoromethyl carbenes; enantioselective cyclopropanation of allenes. Density functional theory calculations clarify the stereoselective and regioselective control mechanisms induced by divergent catalysts. Notably, this work delivers a diverse library of fluoroalkylated methylenecyclopropanes, alkylidenecyclopropanes and chiral analogues, creating new opportunities for organic synthesis and drug discovery.<\/jats:p>","DOI":"10.1021\/jacs.6c08821","type":"journal-article","created":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T21:15:01Z","timestamp":1788297301000},"page":"37945-37953","source":"Crossref","is-referenced-by-count":1,"title":["Allene Cyclopropanation\nwith Fluoroalkyl Carbenes"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8791-6254","authenticated-orcid":true,"given":"Yongquan","family":"Ning","sequence":"first","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ge","family":"Yin","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qianfei","family":"Yu","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaolong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuting","family":"Liu","sequence":"additional","affiliation":[{"name":"University of Amsterdam , Nieuwe Achtergracht 166 , ,","place":["Amsterdam, Netherlands, 1018 WV"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liangliang","family":"Li","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2225-0054","authenticated-orcid":true,"given":"Paramasivam","family":"Sivaguru","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9951-8675","authenticated-orcid":true,"given":"Zhaohong","family":"Liu","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Graham","family":"de Ruiter","sequence":"additional","affiliation":[{"name":"Technion \u2212 Israel Institute of Technology , , , , ,","place":["Technion City, Haifa, Israel, 3200008"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6694-6742","authenticated-orcid":true,"given":"Xihe","family":"Bi","sequence":"additional","affiliation":[{"name":"Northeast Normal University , , ,","place":["Changchun, China, 130024"]},{"name":"Nankai University , , ,","place":["Tianjin, China, 300071"]},{"name":"Nanjing University , , ,","place":["Nanjing, China, 210093"]},{"name":"Yangzhou University , , , ,","place":["Yangzhou, Jiangsu, China, 225002"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,27]]},"reference":[{"key":"2026090910081066400_cit1","doi-asserted-by":"publisher","first-page":"11651","DOI":"10.1021\/acs.chemrev.6b00798","article-title":"Cyclopropanation strategies in recent total syntheses","volume":"117","author":"Ebner","year":"2017","journal-title":"Chem. 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