title: Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.
abstract: The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607-7061, United States.
authors.forename: Anton V
authors.initials: AV
authors.lastname: Gulevich
authors.forename: Ferdinand S
authors.initials: FS
authors.lastname: Melkonyan
authors.forename: Dhruba
authors.initials: D
authors.lastname: Sarkar
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry*; D017655:Silicon Compounds / Q000737:chemistry*
chemical_list: D006841:Hydrocarbons, Aromatic; D012118:Resorcinols; D017655:Silicon Compounds; D010165:Palladium; D010100:Oxygen; C031389:resorcinol