{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T20:59:28Z","timestamp":1781643568192,"version":"3.54.5"},"reference-count":177,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2024,7,2]],"date-time":"2024-07-02T00:00:00Z","timestamp":1719878400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Electron-rich heteroaromatics, such as furan, thiophene and pyrrole, as well as their benzo-condensed derivatives, are of great interest as components of natural products and as starting substances for various products including high-tech materials. Although their reactions with Br\u00f8nsted and Lewis acids play important roles, in particular as the primary step of various transformations, they are often disregarded and mechanistically not understood. The present publication gives a first overview about this chemistry focusing on the parent compounds. It comprises reactions with strong Br\u00f8nsted acids forming adducts that can undergo intramolecular proton and\/or substituent transfer reactions, ring openings or ring transformations into other heterocycles, depending on their structure. Interactions with weak Br\u00f8nsted acids usually initiate oligomerizations\/polymerizations. A similar behaviour is observed in reactions of these heteroaromatics with Lewis acids. Special effects are achieved when the Lewis acids are activated through primary protonation. Deuterated Br\u00f8nsted acids allow straight forward deuteration of electron-rich heteroaromatics. Mercury salts as extremely weak Lewis acids cause direct metalation in a straight forward way replacing ring H-atoms yielding organomercury heterocycles. This review will provide comprehensive information about the chemistry of adducts of such heterocycles with Br\u00f8nsted and Lewis acids enabling chemists to understand the mechanisms and the potential of this field and to apply the findings in future syntheses.<\/jats:p>","DOI":"10.3390\/molecules29133151","type":"journal-article","created":{"date-parts":[[2024,7,2]],"date-time":"2024-07-02T09:01:39Z","timestamp":1719910899000},"page":"3151","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Formation and Reactions of Br\u00f8nsted and Lewis Acid Adducts with Electron-Rich Heteroaromatic Compounds"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4518-9295","authenticated-orcid":false,"given":"Horst","family":"Hartmann","sequence":"first","affiliation":[{"name":"Fakult\u00e4t Chemie und Lebensmittelchemie, Technische Universit\u00e4t Dresden, 01069 Dresden, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1802-5543","authenticated-orcid":false,"given":"J\u00fcrgen","family":"Liebscher","sequence":"additional","affiliation":[{"name":"National Institute for Research and Development of Isotopic and Molecular Technologies INCDTIM, 400293 Cluj-Napoca, Romania"},{"name":"Institute of Chemistry, Humboldt-University of Berlin, 12489 Berlin, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,2]]},"reference":[{"key":"ref_1","unstructured":"Taylor, R.J.K. 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