{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T17:38:12Z","timestamp":1790444292073,"version":"4.1.0"},"reference-count":47,"publisher":"Wiley","issue":"31","license":[{"start":{"date-parts":[[2023,6,23]],"date-time":"2023-06-23T00:00:00Z","timestamp":1687478400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100019180","name":"HORIZON EUROPE European Research Council","doi-asserted-by":"publisher","award":["101040025"],"award-info":[{"award-number":["101040025"]}],"id":[{"id":"10.13039\/100019180","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021856","name":"Ministero dell'Universit\u00e0 e della Ricerca","doi-asserted-by":"publisher","award":["2020927WY3_002"],"award-info":[{"award-number":["2020927WY3_002"]}],"id":[{"id":"10.13039\/501100021856","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Here, we report a general approach to the synthesis of the difluoroalkyl bicycloalkanes (CF\n                    <jats:sub>2<\/jats:sub>\n                    \u2010BCAs), as structural surrogates of aryl ketones and ethers. The chemistry is driven by a dihydrobenzoacridine photocatalyst, that engages in a catalytic electron\u2010donor acceptor (EDA) complex, or directly reduces the fluorinated substrate. These two convergent manifolds lead to the generation of the R\u2010CF\n                    <jats:sub>2<\/jats:sub>\n                    radical, that reacts with the [1.1.1]\u2010 or [3.1.1.]\u2010propellane. The method is extremely general, and extendable to complex bioactive molecules (30 examples, up to 87\u2009% yield). The structural features of the CF\n                    <jats:sub>2<\/jats:sub>\n                    \u2010BCP hybrid bioisostere were investigated by single crystal X\u2010ray. Finally, we synthesised a CF\n                    <jats:sub>2<\/jats:sub>\n                    \u2010BCP analogue of a Leukotriene A\n                    <jats:sub>4<\/jats:sub>\n                    hydrolase inhibitor, replacing the original aryl ether motif. In silico docking studies indicated that this new analogue maintains the same arrangement within the enzyme pocket, profiling the use of the CF\n                    <jats:sub>2<\/jats:sub>\n                    \u2010BCA hybrid bioisostere in medicinal chemistry settings.\n                  <\/jats:p>","DOI":"10.1002\/anie.202303585","type":"journal-article","created":{"date-parts":[[2023,6,1]],"date-time":"2023-06-01T07:09:06Z","timestamp":1685603346000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":50,"title":["A General Organophotoredox Strategy to Difluoroalkyl Bicycloalkane (CF2\u2010BCA) Hybrid Bioisosteres**"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6179-7306","authenticated-orcid":false,"given":"Sara","family":"Cuadros","sequence":"first","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4826-1499","authenticated-orcid":false,"given":"Giulio","family":"Goti","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8125-3293","authenticated-orcid":false,"given":"Giorgia","family":"Barison","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alfredo","family":"Raulli","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7522-9756","authenticated-orcid":false,"given":"Tommaso","family":"Bortolato","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giorgio","family":"Pelosi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Science 17 43124 Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paolo","family":"Costa","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0423-9628","authenticated-orcid":false,"given":"Luca","family":"Dell'Amico","sequence":"additional","affiliation":[{"name":"Department of Chemical Sciences University of Padova  Via Francesco Marzolo 1 35131 Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6,23]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm1013693"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.6b00043"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01788"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00746"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm990496z"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02812E"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.7b00018"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC02880D"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211892"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0021-z"},{"key":"e_1_2_7_13_1","unstructured":"\u00a0"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.9b00287"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00648"},{"key":"e_1_2_7_16_1","unstructured":"\u00a0"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c01416"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02386"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c03498"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00360G"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00487"},{"key":"e_1_2_7_22_1","unstructured":"\u00a0"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201912455"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c00565"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c11364"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c00604"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b03190"},{"key":"e_1_2_7_28_1","unstructured":"\u00a0"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b13920"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201901168"},{"key":"e_1_2_7_31_2","volume":"27","author":"Roth H. G.","year":"2016","journal-title":"Synlett"},{"key":"e_1_2_7_32_1","unstructured":"\u00a0"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC05467A"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja108560e"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200961"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01699"},{"key":"e_1_2_7_37_1","unstructured":"Deposition Numbers2226178 (for17) 2217587 (for26) 2226179 (for35) and 2217588 (for39)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_38_1","unstructured":"Data available in the CCDC database:https:\/\/www.ccdc.cam.ac.uk\/."},{"key":"e_1_2_7_39_1","unstructured":"\u00a0"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00795"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704146"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/B613014N"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr050992x"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC01355A"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00325"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1402136111"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm900259h"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202303585","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,19]],"date-time":"2023-08-19T01:18:33Z","timestamp":1692407913000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202303585"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,6,23]]},"references-count":47,"journal-issue":{"issue":"31","published-print":{"date-parts":[[2023,8]]}},"alternative-id":["10.1002\/anie.202303585"],"URL":"https:\/\/doi.org\/10.1002\/anie.202303585","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv-2023-vdvlw","asserted-by":"object"}]},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,6,23]]},"assertion":[{"value":"2023-03-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-06-23","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202303585"}}