{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T20:29:48Z","timestamp":1788812988444,"version":"build-2803163510"},"reference-count":49,"publisher":"Wiley","issue":"16","license":[{"start":{"date-parts":[[2025,7,12]],"date-time":"2025-07-12T00:00:00Z","timestamp":1752278400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,7,12]],"date-time":"2025-07-12T00:00:00Z","timestamp":1752278400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100004770","name":"Universit\u00e0 degli Studi di Parma","doi-asserted-by":"publisher","award":["Bando di Ateneo 2024 per la ricerca\u2013Azione C"],"award-info":[{"award-number":["Bando di Ateneo 2024 per la ricerca\u2013Azione C"]}],"id":[{"id":"10.13039\/501100004770","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003407","name":"Ministero dell\u2019Istruzione, dell\u2019Universit\u00e0 e della Ricerca","doi-asserted-by":"publisher","award":["20223B4JWC"],"award-info":[{"award-number":["20223B4JWC"]}],"id":[{"id":"10.13039\/501100003407","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003407","name":"Ministero dell\u2019Istruzione, dell\u2019Universit\u00e0 e della Ricerca","doi-asserted-by":"publisher","award":["COMP\u2010HUB & COMP\u2010R initiatives"],"award-info":[{"award-number":["COMP\u2010HUB & COMP\u2010R initiatives"]}],"id":[{"id":"10.13039\/501100003407","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003407","name":"Ministero dell\u2019Istruzione, dell\u2019Universit\u00e0 e della Ricerca","doi-asserted-by":"publisher","award":["Departments of Excellence"],"award-info":[{"award-number":["Departments of Excellence"]}],"id":[{"id":"10.13039\/501100003407","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2025,8,6]]},"abstract":"<jats:p>Five\u2010membered heterocycles such as pyrroles and thiophenes, along with cyclopentenones, are key scaffolds in pharmaceutical chemistry. However, the synthesis of these motifs via diversity oriented synthesis is hindered by the limited accessibility of unsymmetrical 1,4\u2010diketones. Herein, a practical and sustainable flow protocol is presented for the telescoped synthesis of pyrroles, thiophenes, and cyclopentenones. The process begins with decatungstate\u2010photocatalyzed hydrogen atom transfer from aldehydes to generate acyl radicals, which undergo regioselective addition to functionalized enones. The resulting diketones are then fed into a second reactor\u2014tubular or packed\u2010bed\u2014to undergo Paal\u2013Knorr or Hunsdiecker condensation reactions. This modular strategy enables rapid access to densely substituted, biorelevant hetero\u2010 and carbocycles with unconventional substitution patterns, as demonstrated by the synthesis of tri\u2010, tetra\u2010, and pentasubstituted pyrroles and thiophenes, and mono\u2010, di\u2010, and trisubstituted cyclopentenones.<\/jats:p>","DOI":"10.1002\/cssc.202501012","type":"journal-article","created":{"date-parts":[[2025,6,20]],"date-time":"2025-06-20T08:03:13Z","timestamp":1750406593000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["A Telescoped Strategy for the Preparation of Five\u2010Membered Hetero\u2010 and Carbocycles via Hydrogen Atom Transfer Photocatalysis in Flow"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-6701-8149","authenticated-orcid":false,"given":"Filippo","family":"Sacchelli","sequence":"first","affiliation":[{"name":"SynCat Lab Department of Chemistry Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Scienze 17\/A 43124 Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-0598-7303","authenticated-orcid":false,"given":"Elena","family":"Quadri","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab Department of Chemistry University of Pavia  viale Taramelli 12 27100 Pavia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-7975-7183","authenticated-orcid":false,"given":"Luna","family":"Raineri","sequence":"additional","affiliation":[{"name":"SynCat Lab Department of Chemistry Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Scienze 17\/A 43124 Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5200-2735","authenticated-orcid":false,"given":"Alexandra","family":"Jorea","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab Department of Chemistry University of Pavia  viale Taramelli 12 27100 Pavia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marzia","family":"Pessina","sequence":"additional","affiliation":[{"name":"SynCat Lab Department of Chemistry Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Scienze 17\/A 43124 Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Lo Presti","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab Department of Chemistry University of Pavia  viale Taramelli 12 27100 Pavia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicola","family":"Della Ca\u2019","sequence":"additional","affiliation":[{"name":"SynCat Lab Department of Chemistry Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Scienze 17\/A 43124 Parma Italy"},{"name":"CIRCC (Interuniversity Consortium Chemical Reactivity and Catalysis)  via Celso Ulpiani 27 70126 Bari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2201-4828","authenticated-orcid":false,"given":"Davide","family":"Ravelli","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab Department of Chemistry University of Pavia  viale Taramelli 12 27100 Pavia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7114-267X","authenticated-orcid":false,"given":"Luca","family":"Capaldo","sequence":"additional","affiliation":[{"name":"SynCat Lab Department of Chemistry Life Sciences and Environmental Sustainability University of Parma  Parco Area delle Scienze 17\/A 43124 Parma Italy"},{"name":"CIRCC (Interuniversity Consortium Chemical Reactivity and Catalysis)  via Celso Ulpiani 27 70126 Bari Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,12]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202300447"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/ph14070692"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00255a001"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2023.133747"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60015G"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules191015687"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18850180175"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18840170220"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500387"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19420750502"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470638859.conrr337"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00179-1"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms1081"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197300811"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197606391"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja904375q"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202000378"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b03719"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03840"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02392"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810798"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809601"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610329"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC03810D"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)89026-7"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604820"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201500483"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02112E"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO01973C"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC00992K"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c00644"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202400781"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00707"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC01581A"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1080\/01614940.2018.1529932"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1080\/10406638.2023.2225676"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SU00395G"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/op100338z"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25407g"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306468"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RE00081A"},{"key":"e_1_2_7_43_1","unstructured":"The calculation was reported on the radical addition of heptanal to cyclohexenone."},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.5c00530"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob00066c"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr040650b"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00005a007"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja804159y"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00929a052"},{"key":"e_1_2_7_50_1","unstructured":"Prices of symmetrical diketones are based on BLDPharm Hexane\u20102 5\u2010dione [110\u201013\u20104] https:\/\/www.bldpharm.com\/products\/110\u201013\u20104.html (accessed May 6 2025). Octane\u20103 6\u2010dione [2955\u201065\u20109] https:\/\/www.bldpharm.com\/products\/2955\u201065\u20109.html (accessed May 6 2025). 1 4\u2010Diphenylbutane\u20101 4\u2010dione [495\u201071\u20106] https:\/\/www.bldpharm.com\/products\/495\u201071\u20106.html (accessed May 6 2025). Prices of unsymmetrical diketones are based on Enamine 1\u2010cyclopropylpentane\u20101 4\u2010dione [167692\u201057\u20101] https:\/\/new.enaminestore.com\/catalog\/BBV\u201033911276 (accessed May 6 2025). 1\u2010(oxan\u20103\u2010yl)pentane\u20101 4\u2010dione [77342\u201068\u20108] https:\/\/new.enaminestore.com\/catalog\/BBV\u201037842012 (accessed May 6 2025). 1\u2010(4\u2010chlorophenyl)pentane\u20101 4\u2010dione [53842\u201012\u20109] https:\/\/new.enaminestore.com\/catalog\/BBV\u201027034564 (accessed May 6 2025). 1\u2010cyclohexylpentane\u20101 4\u2010dione [61771\u201079\u20107] https:\/\/new.enaminestore.com\/catalog\/BBV\u201033910872 (accessed May 6 2025). Prices converted to euros as of May 6 2025."}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202501012","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cssc.202501012","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202501012","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T08:50:24Z","timestamp":1780563024000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.202501012"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,12]]},"references-count":49,"journal-issue":{"issue":"16","published-print":{"date-parts":[[2025,8,6]]}},"alternative-id":["10.1002\/cssc.202501012"],"URL":"https:\/\/doi.org\/10.1002\/cssc.202501012","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,12]]},"assertion":[{"value":"2025-05-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202501012"}}