title: Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate.
abstract: [reaction: see text] Dirhodium caprolactamate [Rh2(cap)4] is an effective catalyst for benzylic oxidation with tert-butyl hydroperoxide (TBHP) under mild conditions. Sodium bicarbonate is the optimal base additive for substrate conversion. Benzylic carbonyl compounds are readily obtained, and a formal synthesis of palmarumycin CP2 using this methodology is described.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Arthur J
authors.initials: AJ
authors.lastname: Catino
authors.forename: Jason M
authors.initials: JM
authors.lastname: Nichols
authors.forename: Hojae
authors.initials: H
authors.lastname: Choi
authors.forename: Sidhartha
authors.initials: S
authors.lastname: Gottipamula
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D013141:Spiro Compounds
chemical_list: D001555:Benzene Derivatives; D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; D009942:Organometallic Compounds; D013141:Spiro Compounds; C462859:palmarumycin CP2; D012238:Rhodium