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This gave stable magnesium ketyl complexes which are monomeric, [(<jats:sup>Ar<\/jats:sup>Nacnac)(DMAP)Mg(fluor\u22c5)] (Ar=Mes or Dip, DMAP=4\u2010dimethylaminopyridine) and [(<jats:sup>Mes<\/jats:sup>Nacnac)Mg(xanth\u22c5)(xanth)]; dimeric, [{(<jats:sup>Mes<\/jats:sup>Nacnac)Mg(\u03bc\u2010fluor\u22c5)}<jats:sub>2<\/jats:sub>], or tetrameric, [{(<jats:sup>Dip<\/jats:sup>Nacnac)Mg(\u03bc\u2010anth\u22c5)}<jats:sub>4<\/jats:sub>]. In contrast, di\u20102\u2010pyridylketone (OCPy<jats:sub>2<\/jats:sub>) is doubly reduced with [{(<jats:sup>Xyl<\/jats:sup>Nacnac)Mg}<jats:sub>2<\/jats:sub>] (Xyl=xylyl) to give a diamagnetic alkoxy\/amido complex, [{(<jats:sup>Xyl<\/jats:sup>Nacnac)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010OCPy<jats:sub>2<\/jats:sub>)]. These complexes have been characterized by X\u2010ray crystallography, and in three cases, EPR spectroscopy. Regioselective C\u2212C hetero\u2010coupling reactions between magnesium ketyls and phenanthroline (phen) have yielded the alkoxy compounds, [(<jats:sup>Mes<\/jats:sup>Nacnac)Mg(OCR<jats:sub>2<\/jats:sub>\u20102\u2010phen)] (OCR<jats:sub>2<\/jats:sub>=xanth, OCPh<jats:sub>2<\/jats:sub> or OC(Ph)(2\u2010Me\u2212Ph)). In addition, homo\u2010 C\u2212C couplings of the enones, chalcone (chalc) and dibenziylideneactetone (DBA), using magnesium(I) reducing agents, have afforded dimagnesium enolates, [{(<jats:sup>Ar<\/jats:sup>Nacnac)(THF)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010chalc<jats:sub>2<\/jats:sub>)] (Ar=Mes or Xyl) and [{(<jats:sup>Dip<\/jats:sup>Nacnac)(THF)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010DBA<jats:sub>2<\/jats:sub>)]. A pinacol coupling reaction between [{(<jats:sup>Dip<\/jats:sup>Nacnac)Mg}<jats:sub>2<\/jats:sub>] and 2\u2010adamantanone (OAd) yielded [{(<jats:sup>Dip<\/jats:sup>Nacnac)(OAd)Mg}<jats:sub>2<\/jats:sub>(\u03bc\u2010OAd<jats:sub>2<\/jats:sub>)], presumably via a ketyl intermediate. This study further highlights the utility magnesium(I) compounds have as selective reducing agents in organic transformations.<\/jats:p>","DOI":"10.1002\/chem.202300135","type":"journal-article","created":{"date-parts":[[2023,2,1]],"date-time":"2023-02-01T22:23:12Z","timestamp":1675290192000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Ketyl Radicals Generated from Magnesium(I) Compounds: Useful Reagents for C\u2212C Bond Forming Reactions"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0904-7086","authenticated-orcid":false,"given":"Christopher A.","family":"Rosengarten","sequence":"first","affiliation":[{"name":"School of Chemistry Monash University  PO Box 23 Melbourne VIC, 3800 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