75748-11-7

Upstream product

• 59625-59-1 p-Brom-benzyliden-triphenylphosphoran 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 7150-10-9 4,4'-dibromo-1,2-diphenylethanone 
• 169129-01-5 1,8-bis(4-trimethylsilylcarbonylphenyl)octane 
• 1269230-74-1 3,3-bis(4-bromophenyl)-5,5,6,6-tetramethyl-2-(trimethylsiloxy)-1,4,2-dioxaborinane 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 328931-56-2 4-bromo-N-(2-phenylethyl)benzamide 

Relevant academic research and scientific papers

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.

Ruthenium-Catalyzed Brook Rearrangement Involved Domino Sequence Enabled by Acylsilane-Aldehyde Corporation

A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino sequence is presented to prepare highly functionalized silyloxy indenes with atomic- and step-economy. This domino reaction is triggered by acylsilane-directed C-H activation, and the aldehyde controlled the subsequent enol cyclization/Brook Rearrangement other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyloxy indenes allows access to a diverse range of interesting indene and indanone derivatives.

Palladium-catalyzed carbonylative coupling reactions of aryl iodides with hexamethyldisilane (HMDS) to benzoyl silanes

A novel procedure for the palladium-catalyzed carbonylative synthesis of acyl silanes has been developed. Starting from aryl iodides and hexamethyldisilane (HMDS) various benzoyl silanes are produced in moderate to good yields.

PREPARATION OF SUBSTITUTED BENZOYLTRIMETHYLSILANES BY THE PALLADIUM-CATALYZED SILYLATION OF SUBSTITUTED BENZOYL CHLORIDES WITH HEXAMETHYLDISILANE

A direct preparative route to benzoyltrimethylsilane has been found by the reaction of benzoyl chloride with hexamethyldisilane in the presence of a specified palladium(II) complex as catalyst.