title: Pd(II)-catalyzed ortho- or meta-C-H olefination of phenol derivatives.
abstract: A combination of weakly coordinating auxiliaries and ligand acceleration allows for the development of both ortho- and meta-selective C-H olefination of phenol derivatives. These reactions demonstrate the feasibility of directing C-H functionalizations when functional groups are distal to target C-H bonds. The meta-C-H functionalization of electron-rich phenol derivatives is unprecedented and orthogonal to previous electrophilic substitution of phenols in terms of regioselectivity. These methods are also applied to functionalize α-phenoxyacetic acids, a fibrate class of drug scaffolds.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Hui-Xiong
authors.initials: HX
authors.lastname: Dai
authors.forename: Gang
authors.initials: G
authors.lastname: Li
authors.forename: Xing-Guo
authors.initials: XG
authors.lastname: Zhang
authors.forename: Antonia F
authors.initials: AF
authors.lastname: Stepan
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000085:Acetates; D000475:Alkenes; D009942:Organometallic Compounds; D010636:Phenols; D010165:Palladium; C415326:phenoxyacetic acid