Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant.
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.
Seayad
Jayasree
J
Institute of Chemical and Engineering Sciences, 1 Pesek Road, Singapore 627833. jayasree_seayad@ices.a-star.edu.sg
Seayad
Abdul Majeed
AM
Chai
Christina L L
CL
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
D000085:Acetates; D000475:Alkenes; D004952:Esters; D007462:Iodobenzenes; D009942:Organometallic Compounds; C008857:phenyliodosodiacetate; D003300:Copper