{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T21:12:50Z","timestamp":1790543570894,"version":"4.1.0"},"reference-count":47,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2026,5,2]],"date-time":"2026-05-02T00:00:00Z","timestamp":1777680000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,5,2]],"date-time":"2026-05-02T00:00:00Z","timestamp":1777680000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2026,6,15]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Geminal difunctionalization of carbonyl\u2010derived building blocks represents a versatile strategy for the rapid generation of sp\n                    <jats:sup>3<\/jats:sup>\n                    \u2010rich molecular architectures. In this context, diazo compounds provide a powerful platform for installing two distinct functional groups, yet the reaction space for carbonyl\u2010derived donor\u2013donor diazo systems remains underdeveloped. Here, we report a metal\u2010free migratory insertion of diazo compounds into C\u2500S bonds of sulfonyl cyanides, enabling the simultaneous installation of sulfone and nitrile functionalities at a single carbon center. Key to this transformation is the in situ generation of highly reactive diazo intermediates via photochemical decomposition of bench\u2010stable oxadiazolines derived from ketones. This substantially expands the accessible coupling partner space, previously limited to aldehydes or boronic acids. The reaction exhibits broad functional group, water, and air tolerance, delivers high yields, and provides excellent diastereoselectivity in constrained cyclic systems. Compatibility with both batch and continuous\u2010flow processing, as well as its application to a realistic medicinal chemistry combinatorial library synthesis, highlights the practical utility of the method.\n                  <\/jats:p>","DOI":"10.1002\/anie.6162809","type":"journal-article","created":{"date-parts":[[2026,5,3]],"date-time":"2026-05-03T05:10:42Z","timestamp":1777785042000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Geminal Difunctionalization of Ketones via C\u2500S Bond Insertion of Photogenerated Donor\u2013Donor Diazo Compounds"],"prefix":"10.1002","volume":"65","author":[{"given":"Vincent","family":"George","sequence":"first","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"},{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aryaman","family":"Pattanaik","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel","family":"Maddox","sequence":"additional","affiliation":[{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lukas M.","family":"Sigmund","sequence":"additional","affiliation":[{"name":"Molecular AI, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giovanna","family":"Mejia","sequence":"additional","affiliation":[{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sara","family":"Pahl\u00e9n","sequence":"additional","affiliation":[{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simon O.","family":"Angerer","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Schmoll","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lisa Marie","family":"Schneider","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nidhal","family":"Selmi","sequence":"additional","affiliation":[{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mikhail","family":"Kabeshov","sequence":"additional","affiliation":[{"name":"Molecular AI, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giulia","family":"Bergonzini","sequence":"additional","affiliation":[{"name":"Compound Synthesis and Management, Discovery Sciences BioPharmaceuticals R&amp;D AstraZeneca  M\u00f6lndal Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9241-0637","authenticated-orcid":false,"given":"Julia","family":"Rehbein","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6131-4850","authenticated-orcid":false,"given":"Burkhard","family":"K\u00f6nig","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Pharmacy University of Regensburg  Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,5,2]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00101B"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm901241e"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c01876"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010023\u201037032\u20108"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202208860"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202103606"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301284"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00737F"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201802092"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c05319"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC03581F"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001704"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c02468"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)01856\u20106"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC06202A"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211578"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.328"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200683"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC05678C"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC06537A"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403338s"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470638859"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)96226\u20109"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(01)88524\u20100"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339685"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01828"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02140F"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4GC06330A"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm100762r"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400700"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202401239"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.05.131"},{"key":"e_1_2_8_34_1","doi-asserted-by":"crossref","unstructured":"F. L.Pointner J.Poll E. K.Taskinen et\u00a0al. \u201cMechanistic Study of the Light\u2010Initiated Generation of Free Diazoalkanes: Towards Photo\u2010Orthogonal Synthesis \u201d preprint ChemRxiv April 11 2025 https:\/\/doi.org\/10.26434\/chemrxiv\u20102025\u2010n2fzl.","DOI":"10.26434\/chemrxiv-2025-n2fzl"},{"key":"e_1_2_8_35_1","unstructured":"Deposition Numbers 2463789 2463835 2463837 2463828 2464571 2463820 2463783 2463782 2463790 2463805 2463808 2463815 Contain the Supplementary Crystallographic Data for this Paper. This Data is Provided Free of Charge by the Joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures Service."},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.057.0088"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397917508061446"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201605946"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-025-00877-6"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409318"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00902B"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2017.102"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2022.103892"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710445"},{"key":"e_1_2_8_45_1","unstructured":"RDKit: Open\u2010Source Cheminformatics Version 2023.09.6 https:\/\/www.rdkit.org."},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.21105\/joss.00861"},{"key":"e_1_2_8_47_1","first-page":"2825","article-title":"Scikit\u2010learn: Machine Learning in Python","volume":"12","author":"Pedregosa F.","year":"2011","journal-title":"Journal of Machine Learning Research"},{"key":"e_1_2_8_48_1","first-page":"899","article-title":"Standardizing Substrate Selection: A Strategy Toward Unbiased Evaluation of Reaction Generality","volume":"10","author":"Rana D.","year":"2024","journal-title":"ACS Central Science"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.6162809","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.6162809","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.6162809","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,6,15]],"date-time":"2026-06-15T09:50:40Z","timestamp":1781517040000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.6162809"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,2]]},"references-count":47,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2026,6,15]]}},"alternative-id":["10.1002\/anie.6162809"],"URL":"https:\/\/doi.org\/10.1002\/anie.6162809","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv-2025-j6p2h","asserted-by":"object"}]},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,2]]},"assertion":[{"value":"2026-01-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-03-30","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e6162809"}}