17049-41-1

Usage

Chemical structure

A benzene ring with a phenoxy group and a trimethylsilyl group attached.

Functional groups

Phenoxy and trimethylsilyl groups.

Role in organic synthesis

Commonly used as a reagent in organic synthesis.

Preparation

Used in the preparation of various functionalized organic compounds.

Protecting group

The trimethylsilyl group serves as a protecting group in organic chemistry.

Stabilizing radicals

The phenoxy group is known for its ability to stabilize radicals.

Participation in reactions

The phenoxy group can participate in various types of chemical reactions.

Applications

Used in the synthesis of pharmaceuticals, agrochemicals, and materials science applications.

Versatility

Known for its versatility in chemical reactions and applications.

Stability

Recognized for its stability in various chemical environments.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 101-55-3 4-Bromodiphenyl ether 
• 21473-02-9 4-phenoxyphenylmagnesium bromide 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 108-95-2 phenol 
• 10557-71-8 4-chlorophenyltrimethylsilane 

Downstream Products

• 18870-59-2 10,10-diphenyl-2-trimethylsilanyl-10H-phenoxasiline 
• 133408-73-8 (E)-N-methyl-2-[2-(4-trimethylsilylphenoxy)phenyl]-2-methoxyiminoacetamide 

Relevant academic research and scientific papers

Potassium Hydride as Nucleophile: A Practical Method for Cleavage and Functional Modification of Cr(CO)3-Ar-SiMe3 Bonds

Potassium hydride reacts with Cr(CO)3-aryltrimethylsilanes at room temperature to generate stabilized aryl anions which can further react with electrophiles.

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.

CuI/oxalamide catalyzed couplings of (hetero)aryl chlorides and phenols for diaryl ether formation

Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N-aryl-N′-alkyl-substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N-aryl-N′-alkyl-substituted oxalamides are more effective ligands than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides gave the corresponding coupling products in good yields. Satisfactory conversions were achieved with electron-rich phenols as well as a limited range of electron-poor phenols. Catalyst and ligand loadings as low as 1.5 mol % are sufficient for the scaled-up variants of some of these reactions. Aryl and alkyl: N-Aryl-N′-alkyl-substituted oxalamide ligands promote the CuI catalyzed coupling of (hetero)aryl chlorides and phenols at 120 °C more effectively than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides were converted into the corresponding coupling products in good yields.