title: Overriding ortho-para selectivity via a traceless directing group relay strategy: the meta-selective arylation of phenols.
abstract: The direct functionalization of phenols at the ortho and para position is generally facilitated by the electron-donating nature of the hydroxyl group. Accessing meta-functionalized phenols from the parent phenols, on the other hand, generally requires lengthy synthetic sequences. Here, we report the first methodology for the one-pot direct meta-selective arylation of phenols. This methodology is based on a traceless directing group relay strategy. In this process carbon dioxide is used as a transient directing group which facilitates a palladium catalyzed arylation meta to the phenol hydroxyl group with iodoarenes. This transformation proceeds with complete meta-selectivity and is compatible with a variety of functional groups both in the phenol and in the iodoarene coupling partner.
authors.affiliation: School of Biological and Chemical Sciences, Queen Mary University of London , Joseph Priestley Building, Mile End Road, E1 4NS, London, U.K.
authors.forename: Junfei
authors.initials: J
authors.lastname: Luo
authors.forename: Sara
authors.initials: S
authors.lastname: Preciado
authors.forename: Igor
authors.initials: I
authors.lastname: Larrosa
mesh_terms: D002245:Carbon Dioxide / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010636:Phenols; D002245:Carbon Dioxide; D010165:Palladium