Commercial-Scale Visible Light Trifluoromethylation of 2-Chlorothiophenol Using CF <sub>3</sub> I Gas
Kaid C. Harper, En-xuan Zhang, Zhiqing Liu, Timothy Grieme, Timothy B. Towne, Daniel J. Mack, Jeremy Griffin, Song-yuan Zheng, Ningning Zhang, Srinivas Gangula, Jia-Long Yuan, Robert J. Miller, Pingzhong Huang, James R. Gage, Moiz Diwan, Yi‐Yin Ku
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 the 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 and 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 kg of the desired intermediate and amended to fully continuous manufacturing.