Seeing is Believing: Direct Observation of Reaction Progress in Challenging Systems

Acquiring accurate time-resolved information from a reaction is a critical step when studying any chemical transformation. These data are valuable for both novel transformations to elucidate the reaction mechanism, and with more established processes to identify optimized process conditions. Despite the clear benefit, acquiring accurate data from a reaction can be complicated. Processes involving heterogeneous reaction environments, high pressure, air/water sensitive catalysts or extreme temperatures all provide significant barriers to studying reaction progress in real time.

            In order to study these challenging systems we have developed a prototype reaction platform that utilizes a combination of in-situ reaction monitoring techniques and automated reaction sampling. The tandem application of this suite of process analytical technology allows us to rapidly deconvolute complex pathways and competing reactions. Moreover, these new tools are exceptionally well suited to study transformations that cannot be fully addressed by conventional in situ analytical methods.

This analytical platform has been applied to identify an optimized process to produce the chiral isothiourea catalyst HBTM, and to examine the origin of microwave-specific heating in the allyl-Claisen rearrangements. Current progress on these systems will be discussed.