Commercial-Scale Visible-light Trifluoromethylation of 2-Chlorothiophenol using CF3I gas.

Abstract

Despite the growth of photoredox methods in academia, application of photoredox at scale in the pharmaceutical and fine chemical industries has been slow.In this report, a photoredox trifluoromethylation of a thiophenol was modified from the original literature report and the mechanism was investigated to define key scale-up parameters. The mechanistic insight was leveraged in the design and execution of two different reactor designs: an LED-based plug flow photoreactor as well as a laser-based continuous stirred tank photoreactor. In one of the first examples of commercial scale photoredox chemistry, the process was scaled to provide over 500 kilograms of the desired intermediate and amended to fully continuous manufacturing.

Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis

“…At this early stage in the development of the field, most examples of highly asymmetric photocatalytic reactions have been proof-of-principle academic investigations, and these insights have yet to be translated to commercial applications. As the pharmaceutical industry in particular becomes more interested in the scale-up of photocatalytic processes, , issues concerning maximization of quantum yield and light flux may become more important than they have been to date. Despite the impressive advances that have emerged in the field of asymmetric photocatalysis in recent years, many challenges remain unsolved, perhaps the most important of which is the need for generality.…”