{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,5]],"date-time":"2026-09-05T05:58:34Z","timestamp":1788587914463,"version":"build-2803163510"},"reference-count":95,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2025,7,8]],"date-time":"2025-07-08T00:00:00Z","timestamp":1751932800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["23-73-00003"],"award-info":[{"award-number":["23-73-00003"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>In the chemistry of bio-based furans, the Diels\u2013Alder reaction plays an important role as a renewable route for the synthesis of fuels, fine chemicals, and monomers. Nonetheless, the unfavorable kinetic and thermodynamic parameters inherent to the Diels\u2013Alder reaction involving furans as dienes often lead to the reversibility of cycloaddition, resulting in decreased equilibrium conversion and diastereoselectivity. In this study, we present a new strategy for overcoming the problem of reversibility in chemical reactions. We demonstrate that conducting the reaction under solvent-free conditions can facilitate the transition from a molten state formed by the initial reactants to a solid phase containing the reaction product along with an excess of the initial substrate. According to our results, such a liquid-to-solid transition of the reaction mixture can lead to exceptionally high conversion and diastereoselectivity in the furan\u2013maleimide Diels\u2013Alder reaction, particularly for challenging electron-poor furanic substrates. Our approach enables the reversible furan\u2013maleimide Diels\u2013Alder reaction to be performed in a cleaner and more environmentally friendly manner, free from the complexities associated with the use of solvents and the need for purification from side products.<\/jats:p>","DOI":"10.3390\/ijms26146550","type":"journal-article","created":{"date-parts":[[2025,7,8]],"date-time":"2025-07-08T07:31:57Z","timestamp":1751959917000},"page":"6550","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Overcoming the Reversibility in the Diels\u2013Alder Reaction of Bio-Based Electron-Poor Furans with Maleimides Through Liquid-to-Solid Phase Transition"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7958-1490","authenticated-orcid":false,"given":"Konstantin I.","family":"Galkin","sequence":"first","affiliation":[{"name":"N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, 119991 Moscow, Russia"},{"name":"Center for Project Activities, Moscow Polytechnic University (Moscow Polytech), Bolshaya Semyonovskaya Str., 38,\u00a0107023 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1032-2380","authenticated-orcid":false,"given":"Daria V.","family":"Zakharova","sequence":"additional","affiliation":[{"name":"NTI Center \u201cDigital Materials Science: New Materials and Substances\u201d, Bauman Moscow State Technical University, 2nd Baumanskaya Str., 5, 105005 Moscow, Russia"},{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, bld. 1., 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1402-9878","authenticated-orcid":false,"given":"Rinat R.","family":"Aysin","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, bld. 1., 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0368-2177","authenticated-orcid":false,"given":"Anastasia A.","family":"Danshina","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, bld. 1., 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra M.","family":"Pak","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, bld. 1., 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina V.","family":"Sandulenko","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, bld. 1., 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roman A.","family":"Novikov","sequence":"additional","affiliation":[{"name":"N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1102-2868","authenticated-orcid":false,"given":"Ksenia S.","family":"Egorova","sequence":"additional","affiliation":[{"name":"N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"11055","DOI":"10.1039\/D0CS01382J","article-title":"Trends in the Diels-Alder reaction in polymer chemistry","volume":"50","author":"Briou","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1668","DOI":"10.1002\/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z","article-title":"The Diels-Alder Reaction in Total Synthesis","volume":"41","author":"Nicolaou","year":"2002","journal-title":"Angew. Chem. Int. 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