Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate.
[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.
Catino
Arthur J
AJ
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Nichols
Jason M
JM
Choi
Hojae
H
Gottipamula
Sidhartha
S
Doyle
Michael P
MP
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
D001555:Benzene Derivatives; D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; D009942:Organometallic Compounds; D013141:Spiro Compounds; C462859:palmarumycin CP2; D012238:Rhodium