{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T20:51:45Z","timestamp":1767905505955,"version":"3.49.0"},"reference-count":46,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2024,12,24]],"date-time":"2024-12-24T00:00:00Z","timestamp":1734998400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82304276 82273767"],"award-info":[{"award-number":["82304276 82273767"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Advanced Science"],"published-print":{"date-parts":[[2025,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Given the widespread presence of fluoroalkyl functionalities in bioactive molecules, the development of fluoroalkylation reactions with bench\u2010stable and easy\u2010to\u2010use fluoroalkylating reagents is highly desirable. In addition, realization of mono\u2010, di\u2010, tri\u2010, or polyfluoroalkyation usually requires distinct types of fluoroalkylating reagents under different or even harsh reaction conditions, and a universal method to accomplish different hydrofluoroalkylation of alkenes is lacking. Herein, the use of quaternary fluoroalkyl alcohols is reported as the universal fluoroalkylating reagents to readily facilitate mono\u2010, di\u2010, tri\u2010, or polyfluoroalkylation of a wide range of alkene substrates in high yields. Moreover, a cascade reaction of hydrofluoroalkylation followed by intramolecular fluoroalkylation facilitates the construction of a variety of high\u2010value complex heterocycles bearing diverse fluoroalkyl functionalities from alkenes. Mechanistic studies suggest that a proton\u2010coupled electron transfer (PCET) process may be involved through a radical\u2010generating pathway. The utility of this method is showcased by the late\u2010stage fluoroalkylation of various high\u2010value complex molecules derived from either natural products or drug\u2010like compounds. Of note is that a continuous\u2010flow system is amenable to this homogeneous photoredox conditions, thereby opening up a possibility of using this protocol to realize large\u2010scale manufacturing of fluoroalkyl products with industrial interests.<\/jats:p>","DOI":"10.1002\/advs.202408781","type":"journal-article","created":{"date-parts":[[2024,12,24]],"date-time":"2024-12-24T06:44:17Z","timestamp":1735022657000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Diversified Fluoroalkylation of Alkenes Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents"],"prefix":"10.1002","volume":"12","author":[{"given":"Heng","family":"Lu","sequence":"first","affiliation":[{"name":"Shanghai Frontiers Science Center of Drug Target Identification and Delivery School of Pharmaceutical Sciences Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"National Key Laboratory of Innovative Immunotherapy Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"Frontiers Science Center for Transformative Molecules Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhoulong","family":"Fan","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center of Drug Target Identification and Delivery School of Pharmaceutical Sciences Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"National Key Laboratory of Innovative Immunotherapy Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yike","family":"Zou","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center of Drug Target Identification and Delivery School of Pharmaceutical Sciences Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"National Key Laboratory of Innovative Immunotherapy Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7205-9202","authenticated-orcid":false,"given":"Ao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Shanghai Frontiers Science Center of Drug Target Identification and Delivery School of Pharmaceutical Sciences Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"National Key Laboratory of Innovative Immunotherapy Shanghai Jiao Tong University  Shanghai 200240 China"},{"name":"Frontiers Science Center for Transformative Molecules Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,12,24]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/B610213C"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00392"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01788"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00360G"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2NP00056C"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aat4133"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2733-7"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature11680"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510533"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b08685"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803566"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202004439"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)94447-2"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501052"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509282"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03333"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201912450"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c02606"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202014587"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00074-9"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c05356"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202209029"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812192"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201903801"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-023-01365-0"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202311984"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04542J"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00256"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00374"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609035"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b06517"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202113658"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adj0040"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707171"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b05932"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2022.100763"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c11813"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/open.201402006"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204835"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100085k"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00521"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1527-3466.1992.tb00250.x"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.04.066"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1097\/00000542-195011000-00008"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00662-w"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809984"}],"container-title":["Advanced Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/advs.202408781","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,9]],"date-time":"2025-12-09T14:06:26Z","timestamp":1765289186000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/advs.202408781"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,12,24]]},"references-count":46,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2025,2]]}},"alternative-id":["10.1002\/advs.202408781"],"URL":"https:\/\/doi.org\/10.1002\/advs.202408781","archive":["Portico"],"relation":{},"ISSN":["2198-3844","2198-3844"],"issn-type":[{"value":"2198-3844","type":"print"},{"value":"2198-3844","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,12,24]]},"assertion":[{"value":"2024-07-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-12-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2408781"}}