title: Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation.
abstract: A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.
authors: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors: Chunhui
authors: C
authors: Huang
authors: Nugzar
authors: N
authors: Ghavtadze
authors: Buddhadeb
authors: B
authors: Chattopadhyay
authors: Vladimir
authors: V
authors: Gevorgyan
mesh_terms: D002384:Catalysis; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002396:Catechols; D009942:Organometallic Compounds; D010636:Phenols; D012821:Silanes; C082343:silanol; D010165:Palladium; D010100:Oxygen