Pinacol ester (dimethylphenylsilyl)boronic acid

CAS 185990-03-8, Cat. No EN300-173458

Reagent for boryl substitution

The reagent is capable of transition-metal-free base-mediated boryl substitution of an aryl halide. It is a shelf-stable liquid, well soluble in all common organic solvents. Because of the high cost of the catalyst and the potential for contamination of the product with residual transition-metal impurities, this reagent is a good choice for preparing pharmaceuticals. The reaction exhibits high functional group compatibility and can be applied to substrates bearing ester and amide functional groups. Sterically demanding substrates also undergo the reactions effectively.

Synonyms: 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; (Dimethylphenylsilyl)pinacolborane; (Dimethylphenylsilyl)boronic acid pinacol ester

Selected publication

1. Transition-Metal-Free Synthesis of an Aryl Boronate Ester through Base-Mediated Boryl Substitution of an Aryl Halide with a Silylborane.

Shishido R. Organic Syntheses 2022, 99, 39–52. DOI: 10.15227/orgsyn.099.0039

2. 2-(Dimethylphenylsilyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane.

Ohmura T.; Suginome M. Encyclopedia of Reagents for Organic Synthesis 2011. DOI: 10.1002/047084289X.rn01334