title: Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups.
abstract: The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.
authors.affiliation: Department of Chemistry, Korea University , Anam-ro, Seongbuk-gu, Seoul 136701, Republic of Korea.
authors.forename: Chun-Young
authors.initials: CY
authors.lastname: Lee
authors.forename: Su-Jin
authors.initials: SJ
authors.lastname: Ahn
authors.forename: Cheol-Hong
authors.initials: CH
authors.lastname: Cheon
mesh_terms: D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011522:Protons
chemical_list: D001897:Boronic Acids; D010636:Phenols; D011522:Protons; D001895:Boron; D004121:Dimethyl Sulfoxide