title: A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.
abstract: The coupling of O-pivaloyl benzhydroxamic acids with donor/acceptor diazo compounds provides isoindolones in high yield. The reaction tolerates a broad range of benzhydroxamic acids and diazo compounds, including substituted 2,2,2-trifluorodiazoethanes. Mechanistic experiments suggested that C-H activation is turnover-limiting and irreversible and that insertion of the diazo compound favors electron-deficient substrates.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Todd K
authors.initials: TK
authors.lastname: Hyster
authors.forename: Kyle E
authors.initials: KE
authors.lastname: Ruhl
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D001549:Benzamides; C110621:Isoindol-1-one; D054833:Isoindoles; D007769:Lactams; D009942:Organometallic Compounds; D012238:Rhodium
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