{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T07:59:06Z","timestamp":1791619146986,"version":"4.3.4"},"reference-count":87,"publisher":"Wiley","issue":"63","license":[{"start":{"date-parts":[[2021,10,4]],"date-time":"2021-10-04T00:00:00Z","timestamp":1633305600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,11,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In the context of new scaffolds obtained by photochemical reactions, Patern\u00f2\u2010B\u00fcchi reactions between heteroaromatic, trifluoromethylphenyl ketone and electron rich alkenes to give oxetanes are described. A comprehensive study has then been carried out on the reaction of aromatic ketones with fluorinated alkenes. Depending on the substitution pattern at the oxetane ring, a metathesis reaction is described as a minor side process to give mono fluorinated alkenes. Overall, this last reaction corresponds to a photo\u2010Wittig reaction and yield amid isosteres. In order to explain the uncommon regioselectivity of the Patern\u00f2\u2010B\u00fcchi reaction with these alkenes, electrostatic\u2010potential derived charges (ESP) have been determined. In a second computational study, the relative stabilities of the typical 1,4\u2010diradical intermediates of the Patern\u00f2\u2010B\u00fcchi reaction have been determined. The results well explain the regioselectivity. Further transformations of the oxetanes or previous functionalization of the fluoroalkenes open perspectives for oxetanes as core structures for biologically active compounds.<\/jats:p>","DOI":"10.1002\/chem.202102621","type":"journal-article","created":{"date-parts":[[2021,9,15]],"date-time":"2021-09-15T06:45:00Z","timestamp":1631688300000},"page":"15722-15729","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Studies on The Application of The Patern\u00f2\u2010B\u00fcchi Reaction to The Synthesis of Novel Fluorinated Scaffolds"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7145-1322","authenticated-orcid":false,"given":"Mario Andr\u00e9s","family":"Gomez Fernandez","sequence":"first","affiliation":[{"name":"ICMR Equipe de Photochimie CNRS Universit\u00e9 de Reims Champagne-Ardenne  1 UFR Sciences, B.P. 1039 51687 Reims France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5358-102X","authenticated-orcid":false,"given":"Corentin","family":"Lefebvre","sequence":"additional","affiliation":[{"name":"ICMR Equipe de Photochimie CNRS Universit\u00e9 de Reims Champagne-Ardenne  1 UFR Sciences, B.P. 1039 51687 Reims France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Sudau","sequence":"additional","affiliation":[{"name":"Research &amp; Development Crop Science, Lab 2 Bayer AG  2 Alfred-Nobel-Str. 40789 Monheim Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre","family":"Genix","sequence":"additional","affiliation":[{"name":"Crop Science Division Disease Control Chemistry 2 Bayer S.A.S.  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Building La Dargoire D1 366 69263 Lyon France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2013-4394","authenticated-orcid":false,"given":"Manabu","family":"Abe","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hiroshima University  1-3-1 Kagamiyama Higashi-Hiroshima Hiroshima 739-8526 Japan"},{"name":"Hiroshima Research Center for Photo-Drug-Delivery Systems (Hi\u2212P-DDS)  1-3-1 Kagamiyama Higashi-Hiroshima Hiroshima 739-8526 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8615-7476","authenticated-orcid":false,"given":"Norbert","family":"Hoffmann","sequence":"additional","affiliation":[{"name":"ICMR Equipe de Photochimie CNRS Universit\u00e9 de Reims Champagne-Ardenne  1 UFR Sciences, B.P. 1039 51687 Reims France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,10,4]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"crossref","unstructured":"Special issue: Photochemistry in Organic Synthesis.Chem. 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