{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T12:02:36Z","timestamp":1785499356456,"version":"3.56.0"},"reference-count":50,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T00:00:00Z","timestamp":1785456000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T00:00:00Z","timestamp":1785456000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Herein, we disclose a three\u2010component tandem reaction wherein organoboron and DMSO mediate the ring\u2010opening of cyclopropenones to trigger the subsequent acrylation of alkyl (pseudo)halides. A series of cyclopropenones with various aryl groups, together with diverse alkyl (pseudo)halides bearing primary, secondary, and tosylate\u2010based leaving groups, are converted into trisubstituted\n                    <jats:italic>E<\/jats:italic>\n                    \u2010acrylates under transition metal\u2010free conditions. Using B\n                    <jats:sub>2<\/jats:sub>\n                    pin\n                    <jats:sub>2<\/jats:sub>\n                    as the promoter and Cs\n                    <jats:sub>2<\/jats:sub>\n                    CO\n                    <jats:sub>3<\/jats:sub>\n                    as the base in DMSO at 40\u00b0C, the desired products are obtained in moderate to excellent yields (up to 99%) without the need for exclusion of air or moisture. DMSO serves as both the solvent and the oxygen atom source, while trace amounts of water in the reaction system donates the alkenyl hydrogen atom. The reaction exhibits high functional group tolerance and good scalability, and is applicable to late\u2010stage modification of pharmaceuticals such as indomethacin and naproxen. Furthermore, mechanistic investigations, including isotope labeling experiments and control studies provide insights into the possible mechanistic steps. This formal three\u2010component coupling joins two electrophiles via an exogenous oxygen atom, thus bypassing the need to pre\u2011match electrophiles with nucleophilic partners.\n                  <\/jats:p>","DOI":"10.1002\/chem.71476","type":"journal-article","created":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T11:39:54Z","timestamp":1785497994000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Organoboron\u2010 and DMSO\u2010Mediated Ring\u2010Opening of Cyclopropenones for the Acrylation of Alkyl (Pseudo)Halides"],"prefix":"10.1002","author":[{"given":"Jingyuan","family":"Song","sequence":"first","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xulin","family":"Zeng","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yiming","family":"Luo","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhenzhou","family":"Lu","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoyang","family":"Wen","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jialu","family":"Long","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8745-2752","authenticated-orcid":false,"given":"Bo","family":"Zhang","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Advanced Biomaterials, Department of Biomedical Engineering Southern University of Science and Technology  Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenhui","family":"Hu","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pan\u2010Lin","family":"Shao","sequence":"additional","affiliation":[{"name":"Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target &amp; Clinical Pharmacology, The NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences Guangzhou Medical University  Guangzhou China"},{"name":"Guangdong Provincial Key Laboratory of Advanced Biomaterials, Department of Biomedical Engineering Southern University of Science and Technology  Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,31]]},"reference":[{"key":"e_1_2_7_2_1","volume-title":"Esterification: Methods, Reactions, and Applications","author":"Otera J.","year":"2010"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.aas9319"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20102006\u2010961428"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140\u20106736(04)17514\u20104"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules200610873"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMoa1111170"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejphar.2004.05.031"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4GC01329H"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02612"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc202403007"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03566"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mcat.2022.112228"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.2c01976"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00603"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202401476"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.4c00524"},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1002\/9783527813827.ch9","volume-title":"Nickel Catalysis in Organic Synthesis","author":"Goldfogel M. 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