title: Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle.
abstract: A simple and practical exo-oxime ether auxilixary for ortho-C-H functionalization of aromatic alcohols has been developed. Selective olefination of aromatic alcohols were first achieved via a six- or seven-membered exo-acetone oxime ether palladacycle with broad substrate scope. In addition, the crystal of the exo-palladacycle intermediate was obtained for the first time, and the application of this method in total synthesis of 3-deoxyisoochracinic acid was accomplished via a novel retro-synthetic disconnection approach, thus demonstrating the utility of this transformation.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, PR China.
authors.forename: Kun
authors.initials: K
authors.lastname: Guo
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, PR China.
authors.forename: Xiaolan
authors.initials: X
authors.lastname: Chen
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, PR China.
authors.forename: Mingyu
authors.initials: M
authors.lastname: Guan
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, PR China.
authors.forename: Yingsheng
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D000096:Acetone / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: C576089:3-deoxyisoochracinic acid; D000438:Alcohols; D001572:Benzofurans; D004987:Ethers; D009942:Organometallic Compounds; D010091:Oximes; D000096:Acetone; D010165:Palladium; C035911:acetoxime