51835-45-1

Upstream product

• 35364-99-9 α-chlorobenzyl methyl ether 
• 127-09-3 sodium acetate 
• 538-86-3 benzyl methyl ether 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 64-19-7 acetic acid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 

Downstream Products

• 60669-59-2 ethyl 3-methoxy-3-phenylpropanoate 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 52117-33-6 4-methoxy-4-phenylbutan-2-one 
• 538-86-3 benzyl methyl ether 
• 14629-58-4 trimethyl(phenethyloxy)silane 
• 62559-35-7 5-Phenyl-2,2,8,8-tetramethyl-3,7-dioxa-2,8-disilanonane 

Relevant academic research and scientific papers

Co2(CO)8-catalyzed reactions of acetals or lactones with hydrosilanes and carbon monoxide. A new access to the preparation of 1,2-diol derivatives through siloxymethylation

The Co2(CO)8-catalyzed reaction of acetals with hydrosilanes and CO under mild reaction conditions (an ambient temperature under an ambient CO pressure), leading to the production of vicinal diols is reported. A siloxymethyl group can be introduced via the cleavage of one of two alkoxy groups in the acetal. The effects of the types of hydrosilanes, acetals, solvents, and reaction temperatures on the yield of siloxymethylation products were examined in detail. The reactivity for hydrosilanes is as follows; HSiMe3 > HSiEtMe2 > HSiEt2Me > HSiEt3. Hemiacetal esters are more reactive than dimethyl acetals. The polarity of the solvent used also has a significant effect on both the course of the reaction as well as the reaction rate. The site-selective siloxymethylation can be achieved in the case of cyclic acetals such as tetrahydrofuran (THF) and tetrahydropyrane (THP) derivatives, depending on the nature of the oxygen substituent attached adjacent to the oxygen atom in the ring. When 2-alkoxy THF or THP derivatives are used as substrates, the siloxymethylation takes place with cleavage of the ring C-O bond. In contrast, the reaction of 2-acetoxy THF or THP derivatives results in siloxymethylation with the cleavage of C-OAc bond. The ring-opening siloxymethylation of lactones was also examined.

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ3-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.

Acid catalyzed rearrangement of vinyl and ketene acetals

Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.