{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:52:00Z","timestamp":1792158720463,"version":"4.4.0"},"reference-count":35,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100010712","name":"Viet Nam National University Ho Chi Minh City","doi-asserted-by":"publisher","award":["CB2025-20-13"],"award-info":[{"award-number":["CB2025-20-13"]}],"id":[{"id":"10.13039\/501100010712","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The (3 + 2) cycloaddition of donor\u2013acceptor cyclopropanes (DACs) with carbon\u2013sulfur 2\u03c0 components has become an emerging method to rapidly assemble tetrahydrothiophenes. Starting materials donating the carbon\u2013sulfur unit are often isolated from thionation of carbonyls or carboxylic acid derivatives. Herein we report a method for the cycloaddition of DACs with carbon\u2013sulfur moieties presumably formed in situ via \u03b2-sulfuration of \u03b1-carbonyl sulfoxonium ylides with elemental sulfur. The insertion occurred without the assistance of Lewis acid, perhaps due to the strongly polarized carbon\u2013sulfur-containing intermediate. The hitherto challenging \u03b1-monosubstituted tetrahydrothiophenes were obtained with a wide range of tolerated functionalities.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c04002","type":"journal-article","created":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T03:01:13Z","timestamp":1791255673000},"page":"13094-13097","source":"Crossref","is-referenced-by-count":0,"title":["Insertion into\nDonor\u2013Acceptor Cyclopropanes\nwith Carbon\u2013Sulfur Moieties Derived from Sulfoxonium Ylides\nand Elemental Sulfur"],"prefix":"10.1021","volume":"28","author":[{"given":"Vu H.","family":"Luu","sequence":"first","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dat H.","family":"Tran","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-7258-412X","authenticated-orcid":true,"given":"Tien V.","family":"Le","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hoang V. M.","family":"Trinh","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Khanh T. N.","family":"Ong","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anh T.","family":"Nguyen","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0912-9981","authenticated-orcid":true,"given":"Tung T.","family":"Nguyen","sequence":"additional","affiliation":[{"name":"Ho Chi Minh City University of Technology (HCMUT) , , ,","place":["Ho Chi Minh City, Vietnam, 84"]},{"name":"Vietnam National University Ho Chi Minh City , ,","place":["Ho Chi Minh City, Vietnam, 84"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"key":"2026101608462658200_cit1a","doi-asserted-by":"publisher","first-page":"1067","DOI":"10.1016\/j.bmc.2006.10.016","article-title":"Synthesis of 8-Thiabicyclo[3.2.1]octanes and Their\nBinding Affinity for the Dopamine and Serotonin Transporters","volume":"15","author":"Pham-Huu","year":"2007","journal-title":"Bio. Med. Chem."},{"key":"2026101608462658200_cit1b","doi-asserted-by":"publisher","first-page":"7581","DOI":"10.1021\/acs.joc.5b01177","article-title":"Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis\nof the Thiolane Subunit","volume":"80","author":"Lu","year":"2015","journal-title":"J. Org. Chem."},{"key":"2026101608462658200_cit1c","doi-asserted-by":"publisher","first-page":"14026","DOI":"10.1021\/acs.joc.0c02060","article-title":"Nebulosins:\nTrisubstituted Thiolane Natural Products from the Northeastern Atlantic\nAnnelid Eupolymnia nebulosa","volume":"85","author":"Calabro","year":"2020","journal-title":"J. Org. Chem."},{"key":"2026101608462658200_cit2a","doi-asserted-by":"publisher","first-page":"5314","DOI":"10.1021\/ol302494n","article-title":"Lewis Acid Mediated (3 + 2) Cycloadditions\nof Donor-Acceptor Cyclopropanes With Heterocumulenes","volume":"14","author":"Goldberg","year":"2012","journal-title":"Org. Lett."},{"key":"2026101608462658200_cit2b","doi-asserted-by":"publisher","first-page":"47418","DOI":"10.1039\/C5RA06355H","article-title":"Yb(OTf)3 Catalyzed [3 + 2] Annulations of D\u2013A Cyclopropanes With \u03b2-Oxodithioesters:\nA Regioselective Synthesis of Tetrahydrothiophenes","volume":"5","author":"Wang","year":"2015","journal-title":"RSC Adv."},{"key":"2026101608462658200_cit2c","doi-asserted-by":"publisher","first-page":"14293","DOI":"10.1002\/anie.201708346","article-title":"Stereospecific Reactions\nof Donor\u2013Acceptor Cyclopropanes With Thioketones: Access to\nHighly Substituted Tetrahydrothiophenes","volume":"56","author":"Augustin","year":"2017","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026101608462658200_cit2d","doi-asserted-by":"publisher","first-page":"6062","DOI":"10.1002\/chem.201800957","article-title":"An Expeditious Route\nto trans-Configured Tetrahydrothiophenes Enabled\nby Fe(OTf)3-Catalyzed [3 + 2] Cycloaddition of Donor\u2013Acceptor\nCyclopropanes With Thionoesters","volume":"24","author":"Matsumoto","year":"2018","journal-title":"Chem. Eur.\nJ."},{"key":"2026101608462658200_cit2e","doi-asserted-by":"publisher","first-page":"6250","DOI":"10.1002\/ejoc.202100879","article-title":"Lewis-Acid-Catalyzed\n(3 + 2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes","volume":"2021","author":"Mloston\u0301","year":"2021","journal-title":"Eur. J. Org. Chem."},{"key":"2026101608462658200_cit2f","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.70712","article-title":"Diastereoselective\nSynthesis of Polysubstituted 2-Amidino Thiolanes via Cycloaddition\nof N-Thioacyl Amidines With Donor\u2013Acceptor\nCyclopropanes","volume":"368","author":"Tual","year":"2026","journal-title":"Adv. Synth. Catal."},{"key":"2026101608462658200_cit2g","doi-asserted-by":"publisher","first-page":"820","DOI":"10.1021\/acs.orglett.7b03961","article-title":"Formal\nInsertion of Thioketenes into Donor\u2013Acceptor Cyclopropanes\nby Lewis Acid Catalysis","volume":"20","author":"Augustin","year":"2018","journal-title":"Org. Lett."},{"key":"2026101608462658200_cit3a","doi-asserted-by":"publisher","first-page":"1528","DOI":"10.1021\/acs.accounts.1c00023","article-title":"Exploiting Heavier\nOrganochalcogen\nCompounds in Donor\u2013Acceptor Cyclopropane Chemistry","volume":"54","author":"Augustin","year":"2021","journal-title":"Acc. Chem. 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Asian J."},{"key":"2026101608462658200_cit4a","doi-asserted-by":"publisher","first-page":"1580","DOI":"10.1039\/C8CC09595G","article-title":"Thiourea Participation in [3 + 2]\nCycloaddition with Donor\u2013Acceptor Cyclopropanes: A Domino Process\nto 2-Amino-dihydrothiophenes","volume":"55","author":"Xie","year":"2019","journal-title":"Chem. Commun."},{"key":"2026101608462658200_cit4b","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202424823","article-title":"Halogenated\nDonor\u2013Acceptor Cyclopropanes as Donor\u2013Acceptor Cyclopropene\nSurrogates","volume":"64","author":"Oliver","year":"2025","journal-title":"Angew. Chem., Int. 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Lett."},{"key":"2026101608462658200_cit6c","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.70513","article-title":"Elemental\nSulfur Mediated Cyclization of Amidoximes and Sulfoxonium Ylides to\nAccess 5-Acyl-1,2,4-Oxadiazoles","volume":"15","author":"Le","year":"2026","journal-title":"Asian J. Org.\nChem."},{"key":"2026101608462658200_cit6d","doi-asserted-by":"publisher","first-page":"15358","DOI":"10.1021\/acs.joc.4c01972","article-title":"Pragmatic\nAccess to Hybrid Quinoxaline Scaffold Mediated by Elemental Sulfur\nEnabling Actualization to \u03c0-Extended and Aza-Annulated Heterocyclic\nUnits","volume":"89","author":"Ghosh","year":"2024","journal-title":"J. Org. Chem."},{"key":"2026101608462658200_cit7a","doi-asserted-by":"publisher","first-page":"16782","DOI":"10.1039\/D5CC04089B","article-title":"Visible-Light Photoredox Catalyzed\nThioesterification of Sulfoxonium Ylides with Elemental Sulfur and\n\u03b1-Ketoacids","volume":"61","author":"Wu","year":"2025","journal-title":"Chem. Commun."},{"key":"2026101608462658200_cit7b","doi-asserted-by":"publisher","first-page":"9919","DOI":"10.1021\/acs.orglett.6c02474","article-title":"Construction of Thiophenes\nand Selenophenes via Iron-Promoted [2 + 2+1] Cycloaddition of Alkynes\nwith Elemental Chalcogens","volume":"28","author":"Innami","year":"2026","journal-title":"Org. Lett."},{"key":"2026101608462658200_cit7c","doi-asserted-by":"publisher","first-page":"4297","DOI":"10.1021\/acs.orglett.4c01164","article-title":"Three-Component Assembly of Dihydropyrrolo[3,4-e][1,3]thiazines\nfrom Elemental Sulfur, Maleimides, and 1,3,5-Triazinanes","volume":"26","author":"Wang","year":"2024","journal-title":"Org. Lett."},{"key":"2026101608462658200_cit8","doi-asserted-by":"publisher","first-page":"8588","DOI":"10.1039\/D5SC00125K","article-title":"(3 + 2)-Cycloaddition\nof Bicyclobutanes\nand Thioketones: Access to 2-Thiabicyclo[2.1.1]hexanes without the\nUse of Catalysts or Light","volume":"16","author":"Knyazev","year":"2025","journal-title":"Chem. Sci."},{"key":"2026101608462658200_cit9a","doi-asserted-by":"publisher","first-page":"1192","DOI":"10.1039\/D1SC05708A","article-title":"Asymmetric\nTransformations from Sulfoxonium Ylides","volume":"13","author":"Caiuby","year":"2022","journal-title":"Chem.\nSci."},{"key":"2026101608462658200_cit9b","doi-asserted-by":"publisher","first-page":"758","DOI":"10.1055\/a-2222-3695","article-title":"An Improved\nProtocol for the Synthesis of Carbonyl Sulfoxonium Ylides","volume":"56","author":"de Souza","year":"2024","journal-title":"Synthesis"},{"key":"2026101608462658200_cit10a","doi-asserted-by":"publisher","first-page":"5053","DOI":"10.1002\/ejoc.202101022","article-title":"Electricity\nDriven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: A Mild\nand Straightforward Access to \u03b2-Hydroxy Ketones","volume":"2021","author":"Saha","year":"2021","journal-title":"Eur. J. Org. Chem."},{"key":"2026101608462658200_cit10b","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202419426","article-title":"Photoredox Activation of Donor-Acceptor Cyclopropanes:\nDistonic Radical Cation Reactivity in [3 + 2] Cycloaddition Reactions","volume":"64","author":"Mondal","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101608462658200_cit11","doi-asserted-by":"publisher","first-page":"9609","DOI":"10.1021\/acs.joc.4c01189","article-title":"Mechanisms of the Gewald Synthesis of 2-Aminothiophenes\nfrom Elemental Sulfur","volume":"89","author":"Sharma","year":"2024","journal-title":"J. Org. Chem."},{"key":"2026101608462658200_cit12","doi-asserted-by":"publisher","first-page":"5908","DOI":"10.1039\/D6OB00583G","article-title":"Three-Component\nCyclization of 2-Halonitroarenes, Elemental Sulfur, and Styrenes","volume":"24","author":"Ong","year":"2026","journal-title":"Org. Biomol. Chem."},{"key":"2026101608462658200_cit13","doi-asserted-by":"publisher","first-page":"100086","DOI":"10.1016\/j.tchem.2024.100086","article-title":"Reactivities\nand Mechanisms in Organic Reactions Involving\nActivation of Elemental Sulfur under Basic Conditions","volume":"11","author":"Conen","year":"2024","journal-title":"Tetrahedron Chem."},{"key":"2026101608462658200_cit14","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202200441","article-title":"Molecular\nIodine Mediated Oxidation of Arylated \u03b1-Carbonyl Sulfoxonium\nYlides to 1,2-Dicarbonyl-Containing Compounds","volume":"2022","author":"Echemendi\u0301a","year":"2022","journal-title":"Eur. J. Org. Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c04002","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/doi\/10.1021\/acs.orglett.6c04002\/68751327\/acs.orglett.6c04002.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/doi\/10.1021\/acs.orglett.6c04002\/68751327\/acs.orglett.6c04002.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:14:35Z","timestamp":1792156475000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/41\/13094\/5444887\/Insertion-into-Donor-Acceptor-Cyclopropanes-with"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,5]]},"references-count":35,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,10,5]]},"published-print":{"date-parts":[[2026,10,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c04002","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,5]]}}}