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Their deprotonation gave anions which can be formulated as \u03c0\u2010electron rich anionic N\u2010heterocyclic carbenes. Sulfur and selenium adducts were stabilized as their methyl ethers, and mercury, gold as well as rhodium complexes of the sydnone methide carbenes were prepared. Sydnone methide anions also undergo C\u2212C coupling reactions with 1\u2010fluoro\u20104\u2010iodobenzene under Pd(PPh<jats:sub>3<\/jats:sub>)<jats:sub>4<\/jats:sub> and CuBr catalysis. <jats:sup>77<\/jats:sup>Se\u2005NMR resonance frequencies and <jats:sup>1<\/jats:sup><jats:italic>J<\/jats:italic><jats:sub>C4\u2010Se<\/jats:sub> as well as <jats:sup>1<\/jats:sup><jats:italic>J<\/jats:italic><jats:sub>C4\u2010H<\/jats:sub> coupling constants have been determined to gain knowledge about the electronic properties of the anionic N\u2010heterocyclic carbenes. The carbene carbon atom of the sydnone methide anion <jats:bold>3\u2009j<\/jats:bold> resonates at <jats:italic>\u03b4<\/jats:italic>=155.2\u2005ppm in <jats:sup>13<\/jats:sup>C\u2005NMR spectroscopy at \u221240\u2009\u00b0C which is extremely shifted upfield in comparison to classical N\u2010heterocyclic carbenes.<\/jats:p>","DOI":"10.1002\/anie.202107495","type":"journal-article","created":{"date-parts":[[2021,6,22]],"date-time":"2021-06-22T01:28:36Z","timestamp":1624325316000},"page":"18882-18887","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Sydnone Methides\u2014A Forgotten Class of Mesoionic Compounds for the Generation of Anionic N\u2010Heterocyclic Carbenes"],"prefix":"10.1002","volume":"60","author":[{"given":"Sebastian","family":"Mummel","sequence":"first","affiliation":[{"name":"Clausthal University of Technology Institute of Organic Chemistry  Leibnizstrasse 6 D-38678 Clausthal-Zellerfeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felix","family":"Lederle","sequence":"additional","affiliation":[{"name":"Clausthal University of Technology Institute of Organic Chemistry  Leibnizstrasse 6 D-38678 Clausthal-Zellerfeld Germany"},{"name":"Fraunhofer Heinrich Hertz Institute HHI Fiber Optical Sensor Systems  Am Stollen 19H D-38640 Goslar Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eike G.","family":"H\u00fcbner","sequence":"additional","affiliation":[{"name":"Clausthal University of Technology Institute of Organic Chemistry  Leibnizstrasse 6 D-38678 Clausthal-Zellerfeld Germany"},{"name":"Fraunhofer Heinrich Hertz Institute HHI Fiber Optical Sensor Systems  Am Stollen 19H D-38640 Goslar Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan C.","family":"Namyslo","sequence":"additional","affiliation":[{"name":"Clausthal University of Technology Institute of Organic Chemistry  Leibnizstrasse 6 D-38678 Clausthal-Zellerfeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Nieger","sequence":"additional","affiliation":[{"name":"University of Helsinki Department of Chemistry  P.O. 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