(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&

Physical properties

bp 97–99 C/0.1 mmHg.

Uses

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is widely used as silaboration and silylation reagent for unsaturated organic compounds; a derivative having diethylamino group on the silicon atom for use as a precursor for silylene generation.

Uses

(Dimethylphenylsilyl)boronic acid pinacol ester (Suginome′s reagent) can be used as a reagent:

• For the selective addition of dimethylphenylsilanyl group to cyclic and acyclic unsaturated ketones, esters, acrylonitriles using a copper catalyst.
• In the synthesis of (Z)-4-boryl-1-silyl-2-alkene derivatives by stereoselective addition of silicon-boron bond to acyclic 1,3-dienes in presence of Ni catalyst.
• In the preparation of silyl-substituted butenoate and β-silyl-substituted acrylate derivatives from allenes and propiolate derivatives via hydrosilylation reactions using a copper catalyst.
• In the palladium-catalyzed asymmetric silaboration of allenes and alkanes to offered corresponding β-borylallylsilanes and 2-boryl-1-silylalkanes respectively.

Preparation

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1) is prepared by reaction of dimethylphenylsilyllithium with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, 2 equiv) or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2 equiv).