Since I’m taking a trip to Philadelphia this weekend, I thought I’d share some science news from the city of brotherly love, andalso from my alma mater. Sarah Trice, a doctoral student in the University of Pennsylvania Department of Chemistry, and Professor Gary Molander have developed a new type of reagent to facilitate boronic acid synthesis. Boronic acids are one of the main ingredients of Suzuki-Miyaura cross-coupling reactions, which create carbon-carbon bonds in critical biaryl systems.
Paladium Catalyzed direct boronic acid synthesis from aryl chlorides. Image from JACS.
According to the write up, their new bis-boronic acid will replace the traditional bis(pinacolato)diboron, commonly referred to as BisPin, in the synthesis of pharmaceutical building blocks. It is more efficient, producing less waste and requiring less palladium catalyst. It also uses ethanol as a solvent instead of diethyl ether. Reactions with bis-boronic acids can also proceed at temperatures of 50-80 degrees Celsius compared to the 110 degrees required for reactions with BisPin.
They have decided not to patent their methodology, which they published in JACS, in December of 2010.