107325-71-3

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 135-02-4 ortho-anisaldehyde 
• 24588-70-3 2-(2'-methoxyphenyl)-1,3-dithiane 
• 254973-57-4 2-(2-Methoxyphenyl)-2-(trimethylsilyl)-1,3-dithiane 

Downstream Products

• 1185262-67-2 1-(2-methoxyphenyl)-2-phenyl-2-(trimethylsilyloxy)propan-1-one 
• 5180-78-9 methyl 2-(2-methoxyphenyl)-2-oxoacetate 
• 704-43-8 (2-methoxy-phenyl)-trimethyl-silane 
• 612-16-8 (2-methoxyphenyl)methanol 
• 579-75-9 2-Methoxybenzoic acid 

Relevant academic research and scientific papers

Synthesis of Acylsilanes via Catalytic Dedithioacetalization of 2-Silylated 1,3-Dithianes with 30% Hydrogen Peroxide

Acylsilanes were obtained efficiently from dedithioacetalization of 2-silylated 1,3-dithianes using 30% hydrogen peroxide catalyzed by iron(III) acetylacetonate-sodium iodide. The use of niobium(V) chloride as a catalyst instead of iron(III) acetylacetonate was also effective, except in synthesizing some acyltrimethylsilanes.

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide

Intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide (CO2) was achieved by photoirradiation under catalyst-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of the acylsilanes added to the C═O bond of CO2 to give α-ketocarboxylates, which underwent hydrolysis to afford α-ketocarboxylic derivatives in good yields. Control experiments suggest that the generated siloxycarbene is likely to be from the singlet state (S1) of the acylsilane and the addition to CO2 is not in a concerted manner.

Photochemically promoted transition metal-free cross-coupling of acylsilanes with organoboronic esters

Intermolecular carbon-carbon bond formation between acylsilanes and organoboronic esters was achieved by photoirradiation under almost neutral, transition metal-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of acylsilanes reacted with boronic esters to give the formal B-C bond insertion intermediates, which underwent unique rearrangement to afford the cyclic α-alkoxyboronic esters. Acidic treatment of the resulting crude products under air furnished the cross-coupled ketones in good yields.

Synthesis of acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes mediated by N-bromosuccinimide

The oxidative method for the hydrolysis of 1,3-dithianes was applied to 2-silyl-1,3-dithianes using N-bromosuccinimide providing acylsilanes with good yields under a short reaction period. The oxidation of aroylsilanes to carboxylic acid was prevented by

Enantioselective synthesis of a-hydroxysilanes by bioreduction of aroyltrimcthylsilanes

Aromatic acylsilanes [Ar-CO-SiMe3; Ar = C6H5,4-ClC6H4, 2-, 3- and 4-OMeC6H4, 3,4-(OMe)2C6H3 and 3,4-OCH2OC6H3] were reduced by baker's yeast to optically active a-silyl alcohols in 20-70% yield and 43-88% ee. Comments are made on the influence of silicon in this bioreduction reaction. The Royal Society of Chemistry 1999.