{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T05:53:55Z","timestamp":1778565235037,"version":"3.51.4"},"reference-count":39,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2025,5,7]],"date-time":"2025-05-07T00:00:00Z","timestamp":1746576000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,6,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Herein we report a rapid and efficient method for the synthesis of fused cyclopentenoids via Intramolecular Morita\u2010Baylis\u2010Hillman (IMBH) annulation. In this approach, copper triflate (Cu(OTf)<jats:sub>2<\/jats:sub>) serves as the promoter, favoring cyclization and aromatization over the conventional MBH addition product. A characteristic feature among most of the cyclized product contain two non\u2010separable isomeric mixture of cyclopentene derivatives which has been readily interconverted via 1,5\u2010H shift. This sigmatropic shift has been proved via deuterium labelling experiment using the first synthesized 1\u2010bromo\u20106\u2010methoxy\u20103,4\u2010dihydronaphthalene\u20102\u2010carbaldehyde\u2010d. The equilibration of two cyclopentadiene ring via sigmatropic shift has also been characterized by 2D NMR experiment. The scale\u2010up experiment in the modified IMBH reaction also flourish our protocol significantly. Additionally, the same compounds have also been synthesized in solvent\u2010free conditions using organic acids, which reduces the use of hazardous substances, providing an alternate pathway for the IMBH reaction avoiding conventional aqueous work\u2010up. Moreover, this novel IMBH reaction has been thoroughly investigated and elucidated using Density Functional Theory (DFT). The construction of such fluorescent derivatives and the evaluation of their unique photophysical properties revealed acid\u2010base interactions with active methylene groups, facilitating their use as sensors of hazardous amine derivatives via fluorescence quenching mechanism.<\/jats:p>","DOI":"10.1002\/chem.202501040","type":"journal-article","created":{"date-parts":[[2025,4,29]],"date-time":"2025-04-29T08:55:31Z","timestamp":1745916931000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Copper (II) Triflate\/ Vitamin\u2010C Promoted Modified Morita\u2013Baylis\u2013Hillman Annulation: A Facile Route to Fluorescent Cyclopentene Derivatives"],"prefix":"10.1002","volume":"31","author":[{"given":"Sk Abulkalam","family":"Azad","sequence":"first","affiliation":[{"name":"Department of Chemistry Bidhannagar College  Salt Lake, Sector\u2013I Kolkata 700064 India"},{"name":"Department of Chemistry University of Calcutta  Acharya Prafulla Chandra Road Kolkata 700009 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paritosh","family":"Barik","sequence":"additional","affiliation":[{"name":"Department of Chemistry Bidhannagar College  Salt Lake, Sector\u2013I Kolkata 700064 India"},{"name":"Department of Chemistry University of Calcutta  Acharya Prafulla Chandra Road Kolkata 700009 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jayanta","family":"Samanta","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu 603203 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nayim","family":"Sepay","sequence":"additional","affiliation":[{"name":"Department of Chemistry Lady Brabourne College  Kolkata 700017 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-6208-4648","authenticated-orcid":false,"given":"Amal Tom","family":"Sebastian","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Bombay  Powai Mumbai Maharashtra 400076 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sudipta","family":"Ghara","sequence":"additional","affiliation":[{"name":"Department of Chemistry Bidhannagar College  Salt Lake, Sector\u2013I Kolkata 700064 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Soumen","family":"Giri","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Applied Sciences Kalinga Institute of Industrial Technology (KIIT) Deemed to be University  Bhubaneswar Odisha 751024 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mijanur Rahaman","family":"Molla","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Calcutta  Acharya Prafulla Chandra Road Kolkata 700009 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8353-1306","authenticated-orcid":false,"given":"Debabrata","family":"Maiti","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Bombay  Powai Mumbai Maharashtra 400076 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7173-8681","authenticated-orcid":false,"given":"Shubhankar","family":"Samanta","sequence":"additional","affiliation":[{"name":"Department of Chemistry Bidhannagar College  Salt Lake, Sector\u2013I Kolkata 700064 India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,5,7]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo9715377"},{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja400473v"},{"key":"e_1_2_8_1_3","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc43159b"},{"key":"e_1_2_8_1_4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02343"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7TC05079H"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2017.06.005"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201800389"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2019.04.026"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA13611C"},{"key":"e_1_2_8_4_3","doi-asserted-by":"publisher","DOI":"10.1039\/P19910002479"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27217594"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600811219"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.03.051"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B208778B"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503933"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01981E"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01981E"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA05673E"},{"key":"e_1_2_8_9_3","doi-asserted-by":"publisher","DOI":"10.1039\/B300976A"},{"key":"e_1_2_8_9_4","doi-asserted-by":"publisher","DOI":"10.1021\/ol702694v"},{"key":"e_1_2_8_9_5","first-page":"817","author":"Akagawa K.","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_8_9_6","doi-asserted-by":"publisher","DOI":"10.1021\/jo901468h"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403039b"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo501248e"},{"key":"e_1_2_8_10_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c01396"},{"key":"e_1_2_8_10_4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c01459"},{"key":"e_1_2_8_10_5","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202201188"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC03040D"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40508-016-0051-z"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2NJ01962K"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9NJ05808G"},{"key":"e_1_2_8_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202303287"},{"key":"e_1_2_8_13_4","doi-asserted-by":"publisher","DOI":"10.1039\/D3NJ01991H"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.2174\/2213337207999200726231300"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202400534"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00109"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NJ02356K"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA01745K"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-020-02785-4"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202501040","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T08:46:03Z","timestamp":1760258763000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202501040"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,7]]},"references-count":39,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2025,6,12]]}},"alternative-id":["10.1002\/chem.202501040"],"URL":"https:\/\/doi.org\/10.1002\/chem.202501040","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,7]]},"assertion":[{"value":"2025-03-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-29","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-07","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202501040"}}