{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T15:18:18Z","timestamp":1791299898327,"version":"4.1.0"},"reference-count":89,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T00:00:00Z","timestamp":1784246400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["25K22283"],"award-info":[{"award-number":["25K22283"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["26K00025"],"award-info":[{"award-number":["26K00025"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>An iron-promoted [2+2+1] cycloaddition of alkynes with elemental sulfur and selenium enables the construction of thiophenes and selenophenes. Simple iron compounds, FeI2 and Fe(acac)3, enable these transformations using S8 and Se to afford multisubstituted heterocycles. A range of 1,6-diynes are tolerated, and a three-component variant using terminal and internal alkynes is also available. This protocol provides a practical approach to thiophenes and selenophenes utilizing earth-abundant iron and elemental chalcogens without additional additives.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c02474","type":"journal-article","created":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T16:20:11Z","timestamp":1784305211000},"page":"9919-9925","source":"Crossref","is-referenced-by-count":1,"title":["Construction of Thiophenes and Selenophenes via Iron-Promoted\n[2+2+1] Cycloaddition of Alkynes with Elemental Chalcogens"],"prefix":"10.1021","volume":"28","author":[{"given":"Shurika","family":"Innami","sequence":"first","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mayu","family":"Otani","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kodai","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rikuto","family":"Asai","sequence":"additional","affiliation":[{"name":"Gifu University , , ,","place":["Gifu, Japan, 501-1193"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0000-7304","authenticated-orcid":true,"given":"Kento","family":"Ishida","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0722-4800","authenticated-orcid":true,"given":"Norio","family":"Sakai","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1438-0916","authenticated-orcid":true,"given":"Yohei","family":"Ogiwara","sequence":"additional","affiliation":[{"name":"Tokyo University of Science , , ,","place":["Chiba, Japan, 278-8510"]},{"name":"Gifu University , , ,","place":["Gifu, Japan, 501-1193"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,17]]},"reference":[{"key":"2026080709063127800_cit1","doi-asserted-by":"publisher","first-page":"3036","DOI":"10.1021\/cr500271a","article-title":"Thienothiophenes, Dithienothiophenes,\nand Thienoacenes:\nSyntheses, Oligomers, Polymers, and Properties","volume":"115","author":"Cinar","year":"2015","journal-title":"Chem. Rev."},{"key":"2026080709063127800_cit2","doi-asserted-by":"publisher","first-page":"4322","DOI":"10.1039\/C9RA09712K","article-title":"Recent Developments\nin the Synthesis of Regioregular Thiophene-Based Conjugated Polymers\nfor Electronic and Optoelectronic Applications Using Nickel and Palladium-Based\nCatalytic Systems","volume":"10","author":"Amna","year":"2020","journal-title":"RSC Adv."},{"key":"2026080709063127800_cit3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104026","article-title":"Thiophene-Based\nDerivatives as Anticancer Agents: An Overview on Decade\u2019s Work","volume":"101","author":"Archna","year":"2020","journal-title":"Bioorg. Chem."},{"key":"2026080709063127800_cit4","doi-asserted-by":"publisher","first-page":"2658","DOI":"10.1002\/jhet.3990","article-title":"Thiophene Derivatives:\nA Potent Multitargeted\nPharmacological Scaffold","volume":"57","author":"Singh","year":"2020","journal-title":"J. Heterocyclic Chem."},{"key":"2026080709063127800_cit5","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202100462","article-title":"Thiophene-Containing\nCompounds with Antimicrobial Activity","volume":"355","author":"Roman","year":"2022","journal-title":"Arch.\nPharm."},{"key":"2026080709063127800_cit6","doi-asserted-by":"publisher","first-page":"481","DOI":"10.1039\/D4MD00450G","article-title":"Medicinal\nChemistry-Based Perspectives on Thiophene and Its Derivatives: Exploring\nStructural Insights to Discover Plausible Druggable Leads","volume":"16","author":"Thakur","year":"2025","journal-title":"RSC Med. Chem."},{"key":"2026080709063127800_cit7","doi-asserted-by":"publisher","first-page":"15687","DOI":"10.3390\/molecules191015687","article-title":"Recent Advances in the Synthesis of Thiophene Derivatives\nby Cyclization of Functionalized Alkynes","volume":"19","author":"Mancuso","year":"2014","journal-title":"Molecules"},{"key":"2026080709063127800_cit8","doi-asserted-by":"publisher","first-page":"2571","DOI":"10.1007\/s11030-020-10128-9","article-title":"Recent Strategies in the Synthesis\nof Thiophene Derivatives: Highlights from the 2012\u20132020 Literature","volume":"25","author":"Abedinifar","year":"2021","journal-title":"Mol. Diversity"},{"key":"2026080709063127800_cit9","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202300631","article-title":"Syntheses\nof Thiophenes - Recent Advances","volume":"13","author":"Peng","year":"2024","journal-title":"Asian J. Org.\nChem."},{"key":"2026080709063127800_cit10","doi-asserted-by":"publisher","first-page":"1096","DOI":"10.1080\/10426507.2022.2091566","article-title":"Synthetic Methodologies\nfor the Construction of Selenium-Containing\nHeterocycles: A Review","volume":"197","author":"Saeed","year":"2022","journal-title":"Phosphorus Sulfur Silicon\nRelat. Elem."},{"key":"2026080709063127800_cit11","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202500093","article-title":"Recent Advances\nin the Chemistry of 5 and 6-Membered Selenacycles and Selenaheterocycles","volume":"14","author":"Coelho Dias","year":"2025","journal-title":"Asian J. Org. Chem."},{"key":"2026080709063127800_cit12","doi-asserted-by":"publisher","first-page":"2310","DOI":"10.1021\/ja00215a057","article-title":"Synthesis of Main Group Heterocycles by Metallacycle\nTransfer from Zirconium","volume":"110","author":"Fagan","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"2026080709063127800_cit13","doi-asserted-by":"publisher","first-page":"935","DOI":"10.1021\/ar500429f","article-title":"Conversion of Zirconacyclopentadienes\ninto Metalloles: Fagan\u2013Nugent\nReaction and Beyond","volume":"48","author":"Yan","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026080709063127800_cit14","doi-asserted-by":"publisher","first-page":"1168","DOI":"10.1039\/b915826j","article-title":"Poly(cyclopenta[c]selenophene): A\nNew Polyselenophene","volume":"46","author":"Das","year":"2010","journal-title":"Chem. Commun."},{"key":"2026080709063127800_cit15","doi-asserted-by":"publisher","first-page":"4868","DOI":"10.1021\/jo100756k","article-title":"3,4-Ethylenedioxythiophene\nand 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C\u03b1\u2013Si Bond","volume":"75","author":"Das","year":"2010","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit16","doi-asserted-by":"publisher","first-page":"3930","DOI":"10.1021\/ol101619s","article-title":"Cu-Catalyzed Double S-Alkenylation\nof Potassium Sulfide: A Highly Efficient Method for the Synthesis\nof Various Thiophenes","volume":"12","author":"You","year":"2010","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit17","doi-asserted-by":"publisher","first-page":"1487","DOI":"10.1021\/acs.joc.6b02685","article-title":"Use of Stable Amine-Capped\nPolyynes in the Regioselective Synthesis of Push\u2013Pull Thiophenes","volume":"82","author":"Pigulski","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit18","doi-asserted-by":"publisher","first-page":"4704","DOI":"10.1021\/acs.orglett.8b02066","article-title":"Trisulfur Radical\nAnion (S3\u2022\u2013) Involved [1 + 2 + 2] and [1\n+ 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene\nand 2-Benzylidenetetrahydrothiophene Derivatives","volume":"20","author":"Li","year":"2018","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit19","doi-asserted-by":"publisher","first-page":"5001","DOI":"10.1021\/jo400709s","article-title":"Cu-Catalyzed Synthesis of Diaryl\nThioethers and S-Cycles by Reaction of Aryl Iodides\nwith Carbon Disulfide in the Presence of DBU","volume":"78","author":"Zhao","year":"2013","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit20","doi-asserted-by":"publisher","first-page":"4728","DOI":"10.1021\/acs.orglett.8b01577","article-title":"Radical-Cascade Avenue for 3,4-Fused-Ring-Substituted\nThiophenes","volume":"20","author":"Agrawal","year":"2018","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit21","doi-asserted-by":"publisher","first-page":"13037","DOI":"10.1021\/acs.joc.0c01733","article-title":"Access to\nSubstituted Thiophenes through Xanthate-Mediated Vinyl C(sp2)\u2013Br Bond Cleavage and Heterocyclization of Bromoenynes","volume":"85","author":"Huang","year":"2020","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit22","doi-asserted-by":"publisher","first-page":"15397","DOI":"10.1002\/anie.201609545","article-title":"Catalytic [2 + 2 + 1] Synthesis of\nFused Thiophenes Using Thiocarbonyls as Sulfur Donors","volume":"55","author":"Matsui","year":"2016","journal-title":"Angew., Chem. Int. Ed."},{"key":"2026080709063127800_cit23","doi-asserted-by":"publisher","first-page":"1000","DOI":"10.1021\/acs.orglett.4c04533","article-title":"Radical-Triggered\nBicyclization and Aryl Migration of 1,7-Diynes with Diphenyl Diselenide\nfor the Synthesis of Selenopheno[3,4-c]quinolines","volume":"27","author":"Zhang","year":"2025","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit24","doi-asserted-by":"publisher","first-page":"367","DOI":"10.1021\/cr60301a003","article-title":"Elemental\nSulfur","volume":"76","author":"Meyer","year":"1976","journal-title":"Chem. Rev."},{"key":"2026080709063127800_cit25","doi-asserted-by":"publisher","first-page":"2546","DOI":"10.1002\/asia.201300636","article-title":"Transfer of Sulfur:\nFrom Simple to Diverse","volume":"8","author":"Liu","year":"2013","journal-title":"Chem. - Asian J."},{"key":"2026080709063127800_cit26","doi-asserted-by":"publisher","first-page":"1066","DOI":"10.1002\/adsc.201601329","article-title":"Recent\nAdvances in Organic Reactions Involving Elemental Sulfur","volume":"359","author":"Nguyen","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit27","doi-asserted-by":"publisher","first-page":"477","DOI":"10.1002\/ajoc.201700011","article-title":"Elemental\nSulfur and Molecular Iodine as Efficient Tools for Carbon-Nitrogen\nBond Formation through Redox Reactions","volume":"6","author":"Nguyen","year":"2017","journal-title":"Asian\nJ. Org. Chem."},{"key":"2026080709063127800_cit28","doi-asserted-by":"publisher","first-page":"3448","DOI":"10.1002\/adsc.202000535","article-title":"Recent\nAdvances in the Synthesis of Heterocycles via Reactions Involving\nElemental Sulfur","volume":"362","author":"Nguyen","year":"2020","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.70152","article-title":"Elemental\nSulfur in the Synthesis\nof Organic Compounds (An Update 2019\u20132025)","volume":"368","author":"Chursin","year":"2026","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit30","doi-asserted-by":"publisher","first-page":"5386","DOI":"10.1002\/adsc.202101227","article-title":"Synthesis of Organoselenium\nCompounds with Elemental Selenium","volume":"363","author":"Ma","year":"2021","journal-title":"Adv. Synth.\nCatal."},{"key":"2026080709063127800_cit31","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2022.132752","article-title":"Recent Advances in\nOrganic Synthesis Applying Elemental Selenium","volume":"112","author":"Guo","year":"2022","journal-title":"Tetrahedron"},{"key":"2026080709063127800_cit32","doi-asserted-by":"publisher","first-page":"3249","DOI":"10.1002\/anie.201409468","article-title":"Recent Approaches for the Direct\nUse of Elemental Sulfur in the Synthesis and Processing of Advanced\nMaterials","volume":"54","author":"Lim","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026080709063127800_cit33","doi-asserted-by":"publisher","first-page":"15486","DOI":"10.1002\/anie.201604615","article-title":"Sulfur\nand Its Role in Modern Materials Science","volume":"55","author":"Boyd","year":"2016","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026080709063127800_cit34","doi-asserted-by":"publisher","first-page":"5301","DOI":"10.1021\/ol0523650","article-title":"General Synthesis\nof Thiophene and Selenophene-Based Heteroacenes","volume":"7","author":"Okamoto","year":"2005","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit35","doi-asserted-by":"publisher","first-page":"1351","DOI":"10.1081\/SCC-200057268","article-title":"Microwave-Assisted\nSynthesis of 2-Amino-thiophene-3-Carboxylic Derivatives Under Solvent-Free\nConditions","volume":"35","author":"Huang","year":"2005","journal-title":"Synth. Commun."},{"key":"2026080709063127800_cit36","doi-asserted-by":"publisher","first-page":"2251","DOI":"10.1080\/00397910500184727","article-title":"Heterocyclic\nSynthesis with Nitriles: Synthesis of Some New Thiophene, Pyridazine,\nOxazine, Thiopyran, Pyrrole, and Pyrrolo[1,2-b]pyridazine Derivatives","volume":"35","author":"Abdelrazek","year":"2005","journal-title":"Synth. Commun."},{"key":"2026080709063127800_cit37","doi-asserted-by":"publisher","first-page":"239","DOI":"10.1002\/hc.20291","article-title":"A New Method\nfor the Synthesis of Dinaphtho[1,2-b;2\u2032,1\u2032-d]thiophenes and Selenophenes","volume":"18","author":"Alam","year":"2007","journal-title":"Heteroat.\nChem."},{"key":"2026080709063127800_cit38","doi-asserted-by":"publisher","first-page":"6156","DOI":"10.1021\/ol503015b","article-title":"Trisulfur\nRadical Anion as the Key Intermediate for the Synthesis of Thiophene\nvia the Interaction between Elemental Sulfur and NaOtBu","volume":"16","author":"Zhang","year":"2014","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit39","doi-asserted-by":"publisher","first-page":"8736","DOI":"10.1002\/anie.201503134","article-title":"Conversion of 2-Iodobiaryls\ninto 2,2\u2032-Diiodobiaryls\nvia Oxidation-Iodination Sequences: A Versatile Route to Ladder-Type\nHeterofluorenes","volume":"54","author":"Wu","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026080709063127800_cit40","doi-asserted-by":"publisher","first-page":"10351","DOI":"10.1021\/jacs.6b06486","article-title":"Thiophene-Fused \u03c0-Systems from Diarylacetylenes and Elemental Sulfur","volume":"138","author":"Meng","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026080709063127800_cit41","doi-asserted-by":"publisher","first-page":"5756","DOI":"10.1021\/acs.orglett.6b03078","article-title":"Transition-Metal-Free Diarylannulated Sulfide and Selenide\nConstruction via Radical\/Anion-Mediated Sulfur\u2013Iodine and Selenium\u2013Iodine\nExchange","volume":"18","author":"Wang","year":"2016","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit42","doi-asserted-by":"publisher","first-page":"121","DOI":"10.17344\/acsi.2015.2018","article-title":"Synthesis\nof Novel Arylazothiazolyl-thiophene Dyes for Solar Cell and Nonlinear\nOptical Materials","volume":"63","author":"Khalifa","year":"2016","journal-title":"Acta Chim. Slov."},{"key":"2026080709063127800_cit43","doi-asserted-by":"publisher","first-page":"4858","DOI":"10.1021\/acs.orglett.7b02321","article-title":"DIPEA-Promoted\nReaction of 2-Nitrochalcones with Elemental\nSulfur: An Unusual Approach to 2-Benzoylbenzothiophenes","volume":"19","author":"Nguyen","year":"2017","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit44","doi-asserted-by":"publisher","first-page":"4917","DOI":"10.1021\/acs.orglett.8b02049","article-title":"Thiophene-Fused\nHeteroaromatic Systems Enabled by Internal Oxidant-Induced Cascade\nBis-Heteroannulation","volume":"20","author":"Huang","year":"2018","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit45","doi-asserted-by":"publisher","first-page":"1488","DOI":"10.1039\/C8QO00189H","article-title":"Pd-Catalyzed Disilylation:\nAn Efficient Route to 2,2\u2032-Bis(Trimethylsilyl)Biphenyls via Trapping Transient Dibenzopalladacyclopentadienes with\nHexamethyldisilane","volume":"5","author":"Li","year":"2018","journal-title":"Org. Chem. Front."},{"key":"2026080709063127800_cit46","doi-asserted-by":"publisher","first-page":"387","DOI":"10.1039\/C7GC03437G","article-title":"Sulfurative\nSelf-Condensation of Ketones and Elemental\nSulfur: A Three-Component Access to Thiophenes Catalyzed by Aniline\nAcid\u2013Base Conjugate Pairs","volume":"20","author":"Nguyen","year":"2018","journal-title":"Green Chem."},{"key":"2026080709063127800_cit47","doi-asserted-by":"publisher","first-page":"8630","DOI":"10.1021\/acs.orglett.9b03241","article-title":"Three-Component\nCascade Bis-Heteroannulation of Aryl or Vinyl Methylketoxime Acetates\ntoward Thieno[3,2-c]isoquinolines","volume":"21","author":"Xu","year":"2019","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit48","doi-asserted-by":"publisher","first-page":"9326","DOI":"10.1021\/acs.orglett.9b03396","article-title":"Synthesis\nof 3-HCF2S-Chromones through Tandem Oxa-Michael Addition\nand Oxidative\nDifluoromethylthiolation","volume":"21","author":"Zhang","year":"2019","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit49","doi-asserted-by":"publisher","first-page":"2801","DOI":"10.1039\/C9QO00593E","article-title":"Synthesis\nof Azuleno[2,1-b]thiophenes by Cycloaddition of Azulenylalkynes\nwith Elemental Sulfur and Their Structural, Optical, and Electrochemical\nProperties","volume":"6","author":"Shoji","year":"2019","journal-title":"Org. Chem. Front."},{"key":"2026080709063127800_cit50","doi-asserted-by":"publisher","first-page":"448","DOI":"10.1021\/acs.orglett.9b04206","article-title":"Construction\nof 2-Arylbenzo[4,5]thieno[2,3-d]thiazole Skeleton\nvia CuCl\/S-Mediated Three-Component Reaction","volume":"22","author":"Zhang","year":"2020","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit51","doi-asserted-by":"publisher","first-page":"1726","DOI":"10.1021\/acs.orglett.9b04598","article-title":"Facile Synthesis of 2-Acylthieno[2,3-b]quinolines via Cu-TEMPO-Catalyzed Dehydrogenation, sp2-C\u2013H Functionalization (Nucleophilic Thiolation by S8) of 2-Haloquinolinyl Ketones","volume":"22","author":"Teja","year":"2020","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit52","doi-asserted-by":"publisher","first-page":"1669","DOI":"10.1002\/adsc.202000112","article-title":"Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed\nThree-Component Reaction\nusing Elemental Sulfur","volume":"362","author":"Moon","year":"2020","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit53","doi-asserted-by":"publisher","first-page":"7650","DOI":"10.1021\/acs.orglett.1c02904","article-title":"Photocatalytic\nActivation of Elemental\nSulfur Enables a Chemoselective Three-Component Thioesterification","volume":"23","author":"Murakami","year":"2021","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit54","doi-asserted-by":"publisher","first-page":"3555","DOI":"10.1021\/acs.joc.1c03114","article-title":"Synthesis\nof Substituted\nThiophenes through Dehydration and Heterocyclization of Alkynols","volume":"87","author":"Li","year":"2022","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit55","doi-asserted-by":"publisher","first-page":"945","DOI":"10.1039\/D1NJ05433C","article-title":"Cu-Catalyzed [2 + 2 + 1] Cascade\nAnnulation of Vinyl Iodonium Salts with Elemental Sulfur\/Selenium\nfor the Modular Synthesis of Thiophenes and Selenophenes","volume":"46","author":"Wu","year":"2022","journal-title":"New J. Chem."},{"key":"2026080709063127800_cit56","doi-asserted-by":"publisher","first-page":"5309","DOI":"10.1021\/acs.orglett.2c01907","article-title":"Metal-Free C\u2013S Bond Formation\nin Elemental Sulfur and Cyclobutanol Derivatives: The Synthesis of\nSubstituted Thiophenes","volume":"24","author":"Wu","year":"2022","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit57","doi-asserted-by":"publisher","first-page":"2708","DOI":"10.1039\/D3QO00364G","article-title":"Synthesis\nof 1,4-Dithiins\nand 1,4-Diselenins from Alkynes and Elemental Sulfur\/Selenium under\nTransition Metal-Free Conditions with High Regioselectivity","volume":"10","author":"Cheng","year":"2023","journal-title":"Org. Chem. Front."},{"key":"2026080709063127800_cit58","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2025.134811","article-title":"One-Pot Three-Component\nConstruction of Benzo[4,5]imidazo[1,2-a]benzo[4,5]thieno[3,2-d]pyrimidines through [5 + 1 + 3] Cascade Cyclization","volume":"185","author":"Wang","year":"2025","journal-title":"Tetrahedron"},{"key":"2026080709063127800_cit59","doi-asserted-by":"publisher","first-page":"110","DOI":"10.1016\/j.gresc.2024.09.002","article-title":"Transition Metal-Free\nThiophene Construction\nin Pure Water by Multiplied C\u2013H Functionalization with Enaminones\nand Elemental Sulfur","volume":"7","author":"Tian","year":"2026","journal-title":"Green Synth. Catal."},{"key":"2026080709063127800_cit60","doi-asserted-by":"publisher","first-page":"4725","DOI":"10.1021\/acs.orglett.6c00769","article-title":"Base-Promoted Cascade\nMulticomponent Access to Azatrithiathiophthenes\nfrom Cinnamonitriles, Sulfur and Active Methylhetarenes","volume":"28","author":"Ha","year":"2026","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit61","doi-asserted-by":"publisher","first-page":"7909","DOI":"10.1021\/acs.joc.6c00564","article-title":"S\/Se\/Te\u2013I\nExchange\nof (Vinyl Toluenesulfonate)Benziodolium Salts: Access to Benzo[b]Hetercycles","volume":"91","author":"Liu","year":"2026","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit62","doi-asserted-by":"publisher","first-page":"1276","DOI":"10.1039\/b700812k","article-title":"On the\nStability of 2-Aminoselenophene-3-Carboxylates: Potential Dual-Acting\nSelenium-Containing Allosteric Enhancers of A1 Adenosine\nReceptor Binding","volume":"5","author":"Aumann","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"2026080709063127800_cit63","doi-asserted-by":"publisher","first-page":"4485","DOI":"10.1021\/acs.joc.6b00229","article-title":"Copper-Catalyzed\nThree-Component\nReaction for Regioselective Aryl- and Heteroarylselenation of Indoles\nUsing Selenium Powder","volume":"81","author":"Luo","year":"2016","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit64","doi-asserted-by":"publisher","first-page":"2906","DOI":"10.1021\/acs.joc.6b02865","article-title":"Copper-Catalyzed\nSelenylation of\nImidazo[1,2-a]pyridines with Selenium Powder via\na Radical Pathway","volume":"82","author":"Sun","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit65","doi-asserted-by":"publisher","first-page":"3518","DOI":"10.1021\/acs.orglett.9b00739","article-title":"A Three-Component\nStrategy for Benzoselenophene Synthesis under Metal-Free Conditions\nUsing Selenium Powder","volume":"21","author":"Ni","year":"2019","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit66","doi-asserted-by":"publisher","first-page":"5351","DOI":"10.1002\/adsc.201901023","article-title":"Metal-Free Three-Component\nSelenopheno[2,3-b]indole Formation through Double\nC\u2013H Selenylation with Selenium Powder","volume":"361","author":"Ni","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit67","doi-asserted-by":"publisher","first-page":"5639","DOI":"10.1002\/adsc.202001006","article-title":"Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium\nfor the Synthesis of Selenaheterocycles","volume":"362","author":"Zhang","year":"2020","journal-title":"Adv.\nSynth. Catal."},{"key":"2026080709063127800_cit68","doi-asserted-by":"publisher","first-page":"12494","DOI":"10.1021\/acs.joc.1c00689","article-title":"Polycyclic Arene-Fused Selenophenes\nvia Site Selective Selenocyclization of Arylethynyl Substituted Polycyclic\nArenes","volume":"86","author":"Karmakar","year":"2021","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit69","doi-asserted-by":"publisher","first-page":"19822","DOI":"10.1039\/D3NJ03720G","article-title":"Synthesis\nof Tetrasubstituted Selenophenes by DBU-Induced\nSequential Three-Component Coupling and Intramolecular Cyclization","volume":"47","author":"Wang","year":"2023","journal-title":"New J. Chem."},{"key":"2026080709063127800_cit70","doi-asserted-by":"publisher","first-page":"13042","DOI":"10.1021\/acs.joc.3c01172","article-title":"Silver-Mediated [2 + 2 + 1] Cyclization of ortho-Propioloylbenzonitriles with Elemental Selenium: Synthesis of 4H -indeno[1,2-c][1,2]selenazol-4-ones","volume":"88","author":"Fei","year":"2023","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit71","doi-asserted-by":"publisher","first-page":"C15","DOI":"10.1016\/0022-328X(85)80258-8","article-title":"An \u201cAdduct\u201d between CpRh(S2C2Z2) and ZC\u2261CZ (Z = COOCH3) as an Intermediate in CpRhI-Catalyzed Synthesis of Tetramethyl-2,3,4,5-thiophenetetracarboxylate\nfrom Elemental Sulfur and ZC\u2261CZ","volume":"293","author":"Kajitani","year":"1985","journal-title":"J. Organomet.\nChem."},{"key":"2026080709063127800_cit72","doi-asserted-by":"publisher","first-page":"1960","DOI":"10.1055\/s-0029-1216808","article-title":"An Efficient Synthesis of Tetraalkyl 2,3,4,5-Thiophenetetracarboxylate\nDerivatives","volume":"2009","author":"Alizadeh","year":"2009","journal-title":"Synthesis"},{"key":"2026080709063127800_cit73","doi-asserted-by":"publisher","first-page":"4050","DOI":"10.1002\/adsc.201500422","article-title":"Synthesis\nof Polysubstituted Thiophenes via Base-Induced [2\n+ 2 + 1] Cycloaddition Reaction of Alkynes\nand Elemental Sulfur","volume":"357","author":"Liu","year":"2015","journal-title":"Adv. Synth. Catal."},{"key":"2026080709063127800_cit74","doi-asserted-by":"publisher","first-page":"5911","DOI":"10.1021\/acs.orglett.1c02018","article-title":"Silver-Mediated [2\n+ 2 + 1] Cyclization\nReaction of Diynes with Elemental Selenium\/Sulfur To Synthesize 3,4-Substituted\nCyclopenta[c]Selenophenes\/Cyclopenta[c]Thiophenes","volume":"23","author":"Wang","year":"2021","journal-title":"Org. Lett."},{"key":"2026080709063127800_cit75","doi-asserted-by":"publisher","first-page":"6522","DOI":"10.1039\/D2CC00958G","article-title":"Synthesis of 2,5-Disbustituted\nSelenophenes via a Copper-Catalyzed Regioselective\n[2 + 2 + 1] Cyclization of Terminal Alkynes and Selenium","volume":"58","author":"Zhong","year":"2022","journal-title":"Chem. Commun."},{"key":"2026080709063127800_cit76","doi-asserted-by":"publisher","first-page":"14978","DOI":"10.1021\/acs.joc.3c01438","article-title":"Silver-Mediated Intermolecular [2\n+ 2 + 1] Cyclization of Terminal Alkynones with Elemental Selenium:\nRegioselective Synthesis of 2,4- or 3,4-Dicarbonylselenophenes","volume":"88","author":"He","year":"2023","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit77","doi-asserted-by":"publisher","first-page":"761","DOI":"10.1055\/s-1974-23431","article-title":"The Diyne\nReaction of 1,4-, 1,5-, 1,6-, and 1,7-Diynes via Transition Metal\nComplexes to New Compounds","volume":"1974","author":"Mu\u0308ller","year":"1974","journal-title":"Synthesis"},{"key":"2026080709063127800_cit78","doi-asserted-by":"publisher","first-page":"4549","DOI":"10.1016\/S0040-4039(01)92216-6","article-title":"Cobaltacyclopentadiene Complexes\nas Starting Materials in the Synthesis of Substituted Benzenes, Cyclohexadienes,\nThiophenes, Selenophenes and Pyrroles","volume":"15","author":"Wakatsuki","year":"1974","journal-title":"Tetrahedron\nLett."},{"key":"2026080709063127800_cit79","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202404574","article-title":"Iron-Catalyzed [2 + 2 + 2] Cycloadditions for the Construction\nof Aromatic and Heteroaromatic Rings","volume":"31","author":"Parisot","year":"2025","journal-title":"Chem.\n- Eur. J."},{"key":"2026080709063127800_cit80","doi-asserted-by":"publisher","first-page":"7162","DOI":"10.1002\/anie.201102001","article-title":"A Simple and Highly Efficient Iron\nCatalyst for a [2 + 2 + 2] Cycloaddition to Form Pyridines","volume":"50","author":"Wang","year":"2011","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026080709063127800_cit81","doi-asserted-by":"publisher","first-page":"3065","DOI":"10.1021\/jo400057t","article-title":"Iron-Catalyzed\nCycloaddition Reaction of Diynes and Cyanamides at Room Temperature","volume":"78","author":"Wang","year":"2013","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit82","doi-asserted-by":"publisher","first-page":"41353","DOI":"10.1039\/C4RA06973K","article-title":"Iron-Catalyzed [2 + 2 + 2] Cycloaddition of Trifluoromethyl\nGroup Substituted Unsymmetrical Internal Alkynes","volume":"4","author":"Minakawa","year":"2014","journal-title":"RSC Adv."},{"key":"2026080709063127800_cit83","doi-asserted-by":"publisher","first-page":"7597","DOI":"10.1002\/anie.201502531","article-title":"Synthesis\nof Phosphabenzenes by an Iron-Catalyzed [2 + 2 + 2] Cycloaddition\nReaction of Diynes with Phosphaalkynes","volume":"54","author":"Nakajima","year":"2015","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026080709063127800_cit84","doi-asserted-by":"publisher","first-page":"234","DOI":"10.1021\/acs.joc.6b02374","article-title":"Regioselective\nIron-Catalyzed [2 + 2 + 2] Cycloaddition Reaction Forming 4,6-Disubstituted\n2-Aminopyridines from Terminal Alkynes and Cyanamides","volume":"82","author":"Spahn","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026080709063127800_cit85","doi-asserted-by":"publisher","first-page":"14677","DOI":"10.1021\/acscatal.1c03871","article-title":"Origins of Regio- and Chemoselectivity in Iron-PDAI-Catalyzed\n[2 + 2 + 2] Cycloaddition Syntheses of 4,6-Disubstituted 2-Aminopyridines","volume":"11","author":"Harper","year":"2021","journal-title":"ACS Catal."},{"key":"2026080709063127800_cit86","doi-asserted-by":"publisher","first-page":"18450","DOI":"10.1021\/jacs.2c06993","article-title":"Iron\/Photosensitizer Hybrid System\nEnables the Synthesis\nof Polyaryl-Substituted Azafluoranthenes","volume":"144","author":"Kato","year":"2022","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026080709063127800_cit87","doi-asserted-by":"publisher","first-page":"451","DOI":"10.1016\/S0022-2860(97)00125-7","article-title":"Molecular Structure and Infrared\nSpectra of Furan, Thiophene, Selenophene and Their 2,5-N and 3,4-N\nDerivatives: Density Functional Theory and Conventional post-Hartree\u2013Fock\nMP2 Studies","volume":"436\u2013437","author":"Kwiatkowski","year":"1997","journal-title":"J. Mol. Struct."},{"key":"2026080709063127800_cit88","doi-asserted-by":"publisher","first-page":"7657","DOI":"10.1021\/ja981266x","article-title":"Sulfur-Atom\nTransfer from Elemental Sulfur to Nickel\u2013Carbon\nBonds as a New Route to Reactive Nickel(II) Thiolates","volume":"120","author":"Han","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"2026080709063127800_cit89","doi-asserted-by":"publisher","first-page":"49","DOI":"10.1021\/acs.orglett.0c03674","article-title":"Synthesis of Isothiazoles and Isoselenazoles\nthrough Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur\nand Selenium","volume":"23","author":"Moon","year":"2021","journal-title":"Org. Lett."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c02474","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/31\/9919\/66013664\/acs.orglett.6c02474.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/31\/9919\/66013664\/acs.orglett.6c02474.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,7]],"date-time":"2026-08-07T13:13:29Z","timestamp":1786108409000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/31\/9919\/5214694\/Construction-of-Thiophenes-and-Selenophenes-via"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,17]]},"references-count":89,"journal-issue":{"issue":"31","published-online":{"date-parts":[[2026,7,17]]},"published-print":{"date-parts":[[2026,8,7]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c02474","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,17]]}}}