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This reagent is non\u2010hazardous, easy\u2010to\u2010handle, and in some cases provides access to 1,4\u2010cyclohexadiene reduction products under relatively mild reaction conditions. This system works effectively to reduce benzene, naphthalene and anthracene through magnesium\u2010bound \u201cBirch\u2010type\u201d reduction intermediates. Cyclohexadiene products can be subsequently released from the magnesium centres by protonolysis with methanol. In contrast, the reduction of substituted arenes is less selective and involves competing reaction pathways. For toluene and 1,3,5\u2010triphenylbenzene, the structural authentication of \u201cBirch\u2010type\u201d reduction intermediates is conclusive, although the formation of corresponding 1,4\u2010cyclohexadiene derivatives was low yielding. Reduction of anisole did not yield an isolable \u201cBirch\u2010type\u201d intermediate, but instead gave a C\u2212O activation product. Treating triphenylphosphine with [{K(<jats:sup>TCHP<\/jats:sup>NON)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010N<jats:sub>2<\/jats:sub>)] resulted in the extrusion of both biphenyl and dinitrogen to afford a magnesium(II) phosphanide [{K(<jats:sup>TCHP<\/jats:sup>NON)Mg(\u03bc\u2010PPh<jats:sub>2<\/jats:sub>)}<jats:sub>2<\/jats:sub>]. Reduction of fluorobenzene proceeded <jats:italic>via<\/jats:italic> C\u2212F activation of the arene, and isolation of the magnesium(II) fluoride [{K(<jats:sup>TCHP<\/jats:sup>NON)Mg(\u03bc\u2010F)}<jats:sub>2<\/jats:sub>]. Finally, the two\u2010electron reduction of 1,3,5,7\u2010cyclooctatetraene (COT) with [{K(<jats:sup>TCHP<\/jats:sup>NON)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010N<jats:sub>2<\/jats:sub>)] yielded a complex, [{K(<jats:sup>TCHP<\/jats:sup>NON)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010COT)], incorporating the aromatic dianion (COT<jats:sup>2\u2212<\/jats:sup>).<\/jats:p>","DOI":"10.1002\/chem.202401005","type":"journal-article","created":{"date-parts":[[2024,4,16]],"date-time":"2024-04-16T02:44:24Z","timestamp":1713235464000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Reductions of Arenes using a Magnesium\u2010Dinitrogen Complex"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5383-3220","authenticated-orcid":false,"given":"Matthew J.","family":"Evans","sequence":"first","affiliation":[{"name":"School of Chemistry Monash University  PO Box\u200523 3800 Melbourne Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeremy","family":"Mullins","sequence":"additional","affiliation":[{"name":"School of Chemistry Monash University  PO Box\u200523 3800 Melbourne Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rahul","family":"Mondal","sequence":"additional","affiliation":[{"name":"School of Chemistry Monash University  PO Box\u200523 3800 Melbourne Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7269-1045","authenticated-orcid":false,"given":"Cameron","family":"Jones","sequence":"additional","affiliation":[{"name":"School of Chemistry Monash University  PO Box\u200523 3800 Melbourne Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,5,17]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"See for example"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma2025804"},{"key":"e_1_2_9_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/macp.200700409"},{"key":"e_1_2_9_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01126"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02510-6"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01282a504"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9440000430"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac199668030553"},{"key":"e_1_2_9_9_1","first-page":"1","volume-title":"Organic Reactions","author":"Rabideau P. 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