Sulfones in cross coupling
Developing a method for the use of chiral boranes in the Suzuki-Miyaura reaction to produce chiral products was one of the key developments that came out of work in our group (Jacs 2009 and 2014, and ACIE 2014). This reaction is the number one reaction used in industry for the preparation of carbon-carbon bonds. Prior to our reports, the Suzuki-Miyaura reaction could only be used to make bonds with no stereochemistry, which is a huge limitation since a significant number of pharmaceutical compounds are chiral. We have reported the first example of this reaction performed with chiral organoboron partners, proceeding with retention of chirality.
Building on this work, we have been working with Dr. Masakazu Nambo in Nagoya to develop sulfones as new partners in cross-coupling chemistry. We have reported a variety of processes where sulfones can be used to both increase the functionality of the starting materials and then undergo carbon–carbon or carbon–heteroatom coupling. Current strategies address ways to accomplish this reaction with complex substrates and with the introduction of chirality.