23313-45-3

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 771-98-2 1-Phenylcyclohexene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 4912-59-8 1-phenyl-1,2-cyclohexanediol 

Relevant academic research and scientific papers

BF3·OEt2-promoted diastereoselective diacetoxylation of alkenes by PhI(OAc)2

Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)2/BF3·OEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as α,β-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.

The nature of the catalytically active species in olefin dioxygenation with PhI(OAc)2: Metal or proton?

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.

A microchemical system with continuous recovery and recirculation of catalyst-immobilized magnetic particles

(Figure Presented) Keep on running: A microchemical system for continuous flow catalytic reactions with a magnetic catalyst is presented (see picture). It enables the automatic separation and recirculation of catalyst particles and is applicable to various catalytic reactions.

Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride

A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and nonconjugated olefins.