86551-93-1Relevant articles and documents
Green diacetoxylation of alkenes in a microchemical system
Park, Jeong Hyeon,Park, Chan Yi,Song, Hyun Seung,Huh, Yun Suk,Kim, Geon Hee,Park, Chan Pil
supporting information, p. 752 - 755 (2013/04/10)
The palladium-catalyzed diacetoxylation and trifluoromethanesulfonic acid-catalyzed diacetoxylation using inexpensive and environmentally friendly hydrogen peroxide and peracetic acid were successfully conducted with the help of microchemical technology.
The nature of the catalytically active species in olefin dioxygenation with PhI(OAc)2: Metal or proton?
Kang, Yan-Biao,Gade, Lutz H.
, p. 3658 - 3667 (2011/05/03)
Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)2 as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant
Seayad, Jayasree,Seayad, Abdul Majeed,Chai, Christina L. L.
supporting information; experimental part, p. 1412 - 1415 (2010/06/13)
(Figure Presented) 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.
