{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,1]],"date-time":"2026-08-01T00:13:42Z","timestamp":1785543222275,"version":"3.56.0"},"reference-count":75,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2024,1,10]],"date-time":"2024-01-10T00:00:00Z","timestamp":1704844800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100004319","name":"Pfizer","doi-asserted-by":"publisher","award":["G116121"],"award-info":[{"award-number":["G116121"]}],"id":[{"id":"10.13039\/100004319","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005300","name":"American Chemical Society","doi-asserted-by":"publisher","award":["Arthur C. Cope Award"],"award-info":[{"award-number":["Arthur C. Cope Award"]}],"id":[{"id":"10.13039\/100005300","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2024,2,26]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Sulfonyl groups are widely observed in biologically relevant molecules and consequently, SO<jats:sub>2<\/jats:sub> capture is an increasingly attractive method to prepare these sulfonyl\u2010containing compounds given the range of SO<jats:sub>2<\/jats:sub>\u2010surrogates now available as alternatives to using the neat gas. This, along with the advent of photoredox catalysis, has enabled mild radical capture of SO<jats:sub>2<\/jats:sub> to emerge as an effective route to sulfonyl compounds. Here we report a photoredox\u2010catalyzed cross\u2010electrophile sulfonylation of aryl and alkyl bromides making use of a previously under\u2010used amine\u2010SO<jats:sub>2<\/jats:sub> surrogate; <jats:italic>bis<\/jats:italic>(piperidine) sulfur dioxide (PIPSO). A broad selection of alkyl and aryl bromides were photocatalytically converted to their corresponding sulfinates and then trapped with various electrophiles in a one\u2010pot multistep procedure to prepare sulfones and sulfonamides.<\/jats:p>","DOI":"10.1002\/chem.202303976","type":"journal-article","created":{"date-parts":[[2023,12,20]],"date-time":"2023-12-20T07:00:48Z","timestamp":1703055648000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Photoredox\u2010Catalyzed Preparation of Sulfones Using <i>Bis<\/i>\u2010Piperidine Sulfur Dioxide \u2013 An Underutilized Reagent for SO<sub>2<\/sub> Transfer"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3954-9343","authenticated-orcid":false,"given":"Oliver M.","family":"Griffiths","sequence":"first","affiliation":[{"name":"Yusuf Hamied Department of Chemistry University of Cambridge  Lensfield Road CB2\u20091EW Cambridge UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6932-9005","authenticated-orcid":false,"given":"Henrique A.","family":"Esteves","sequence":"additional","affiliation":[{"name":"Yusuf Hamied Department of Chemistry University of Cambridge  Lensfield Road CB2\u20091EW Cambridge UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Darcy C.","family":"Emmet","sequence":"additional","affiliation":[{"name":"Yusuf Hamied Department of Chemistry University of Cambridge  Lensfield Road CB2\u20091EW Cambridge UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7816-0042","authenticated-orcid":false,"given":"Steven V.","family":"Ley","sequence":"additional","affiliation":[{"name":"Yusuf Hamied Department of Chemistry University of Cambridge  Lensfield Road CB2\u20091EW Cambridge UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,1,10]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.0c00754"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501105n"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.5b00222"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1379042"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201500103"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB02199K"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09759D"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403122a"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol4031233"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705470"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC05847D"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO01073G"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00450b"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01449"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201701194"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900396"},{"key":"e_1_2_9_18_1","first-page":"1166","volume":"49","author":"Li Y.","year":"2020","journal-title":"Chem. Lett."},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201601293"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201601341"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900257"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC06567E"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB02102G"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC00008A"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00163G"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c08218"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c05690"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c07974"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2QO01706G"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c00107"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04722"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC00347A"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-20314-w"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01385"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c08216"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03194"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00060F"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700525"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8QO01048J"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c00559"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01132"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01730"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00558"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04818"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC02253D"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aat4133"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.7b00083"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC00163E"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809493"},{"key":"e_1_2_9_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01193"},{"key":"e_1_2_9_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04180"},{"key":"e_1_2_9_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04610"},{"key":"e_1_2_9_53_1","unstructured":"M.\u2005A. Brodney C.\u2005R. Butler L.\u2005A. McAllister C.\u2005J. Helal S.\u2005V. O'Neil P.\u2005R. Verhoest 1 1 1-Trifluoro-3-Hydroxypropan-2-Yl Carbamate Derivatives As MAGL Inhibitors 2018 US2018\/208607\u2005A1."},{"key":"e_1_2_9_54_1","unstructured":"Y. El-Ahmad B. Filoche-Romme A. Ganzhorm G. Marciniak N. Muzet B. Ronan B. Vivet V. Zerr Pyrimidinone Derivatives as Antimalarial Agents 2013 WO2013190123\u2005A1."},{"key":"e_1_2_9_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202003454"},{"key":"e_1_2_9_56_1","unstructured":"R. Mach S. Reilly M. Makvandi L. Puentes Low Affinity Poly(AD-Ribose) Polymerase 1 Dependent Cytotoxic Agents 2019 WO2019169156\u2005A1."},{"key":"e_1_2_9_57_1","unstructured":"A. Stewart M. Banwell B. Leung A. Augustine J. Kitching T. Bilski Non-Steroidal Compounds 2008 WO2008124878\u2005A1."},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm0611861"},{"key":"e_1_2_9_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/la2047257"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob41837e"},{"key":"e_1_2_9_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00908"},{"key":"e_1_2_9_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700417"},{"key":"e_1_2_9_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.12.076"},{"key":"e_1_2_9_64_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-956487"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201301800"},{"key":"e_1_2_9_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01156"},{"key":"e_1_2_9_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00267"},{"key":"e_1_2_9_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo50011a021"},{"key":"e_1_2_9_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol400472v"},{"key":"e_1_2_9_70_1","first-page":"1463","volume":"26","author":"Truce W. E.","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_9_71_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2021.2016758"},{"key":"e_1_2_9_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01693"},{"key":"e_1_2_9_73_1","unstructured":"W. Fu H. Huang 3-(Dimethylaminomethyl) Cyclohex-4-Alcohol Derivative as Well as Preparation Method and Pharmaceutical Application Thereof 2021 CN112759538\u2005A."},{"key":"e_1_2_9_74_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC06937G"},{"key":"e_1_2_9_75_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2020.151975"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202303976","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:28:39Z","timestamp":1760297319000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202303976"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,10]]},"references-count":75,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2024,2,26]]}},"alternative-id":["10.1002\/chem.202303976"],"URL":"https:\/\/doi.org\/10.1002\/chem.202303976","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,10]]},"assertion":[{"value":"2023-11-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-01-10","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202303976"}}