title: Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant.
abstract: Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.
authors.affiliation: Institute of Chemical and Engineering Sciences, 1 Pesek Road, Singapore 627833. jayasree_seayad@ices.a-star.edu.sg
authors.forename: Jayasree
authors.initials: J
authors.lastname: Seayad
authors.forename: Abdul Majeed
authors.initials: AM
authors.lastname: Seayad
authors.forename: Christina L L
authors.initials: CL
authors.lastname: Chai
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000475:Alkenes; D004952:Esters; D007462:Iodobenzenes; D009942:Organometallic Compounds; C008857:phenyliodosodiacetate; D003300:Copper