Boronic Esters

BoroChem's product catalogue includes an important number of boronic esters. Click here to be redirected to an overview of available boronic esters.

The polar and often amphiphilic character of boronic acids tends to make their isolation and purification difficult. In addition to these potential difficulties in isolating boronic acids, their tendency to form oligomeric anhydrides further complicates characterization efforts. To palliate to these problems, boronic acids are often purified and characterized as boronic esters. Boronic acids are also best handled as ester derivates in case of difficulty in measuring accurate and reproducible melting points for free boronic acids.

For reasons of simplification, the pinacol ester of pyridine-3-ylboronic is called pyridine-3-boronic acid pinacol ester instead of its formal name 3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine.

Advantages of boronic esters

• Easy purification and characterization
• No formation of oligomeric anhydrides
• Enhanced reactivity, thanks to better solubility in organic solvents
• Potential use as protecting groups to eliminate unwanted side reactions
  
  

Main benefits of the use of boronic esters in Suzuki-Miyaura cross-couplings

• Enable the coupling of organoboronic acids that are sensitive to hydrolytic deboronation
  
  

Additional applications of boronic esters

A number of chiral boronic esters, such as the ones illustrated below, have been used as inducers in stereoselective reactions.

Advantages of these boronic esters

• Great stability
• Important enantiomeric excess when used in Matteson homologation
• Easy deprotection

BoroChem's product catalogue includes an important number of boronic esters. Click here to be redirected to an overview of available boronic esters.