CAS 185990-03-8, Cat. No EN300-173458
Reagent for base-mediated borylation
(Dimethylphenylsilyl)boronic acid pinacol ester is a reagent capable of transition-metal-free base-mediated boryl substitution of an aryl halide1. It is a shelf-stable liquid, well soluble in all common organic solvents2. The reagent is a good choice for preparing pharmaceuticals because of the high cost of the catalysts and the potential for contamination of the products with residual transition-metal impurities. The reaction exhibits high functional group compatibility and can be applied to substrates bearing ester and amide functional groups1,2. Sterically demanding substrates also undergo the reaction effectively.
Synonyms: 2-(dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; (dimethylphenylsilyl)pinacolborane; (dimethylphenylsilyl)boronic acid pinacol ester; dimethyl-phenyl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; dimethyl(phenyl)(tetramethyl-1,3,2-dioxaborolan-2-yl)silane
Selected publication
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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
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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