July 3-4, 2023 – Paris, France. The thematic days on continuous flow synthesis are organized each year by the “journées du GDR Synth_Flux“. These GDR Synth_Flux days are an opportunity for all researchers interested in flow chemistry to meet and exchange ideas on the theme of continuous flow technologies. It’s an interdisciplinary event that touches on a wide range of topics, such as organic synthesis, materials chemistry and process engineering, and is as close as possible to industrial issues.
Dr. Sylvain Guizzetti, Associate Director for Flow and Process Chemistry delivered an oral presentation entitled “Development of photocatalyzed reactions under flow conditions” during these days “journées du GDR Synth_Flux.”
Over the last years, the good match between photo- and flow- chemistry had led to an ever-growing number of applications to the fields of drug discovery and API production.1,2 In this context, we have optimized different photochemical reactions under flow conditions to produce building blocks of interest for drug discovery program.
In particular, we have: i) implemented a two-step telescoped synthesis of pyrrole relying on a photochemical Giese addition of xanthates3
; ii) transitioned a recently described protocol for Csp2 -Csp3 bond formation through XAT4 , iii) optimized difluoroamidation of indoles to provide gram-scale quantities and demonstrate the possibility of focused library synthesis via a two-step telescoped sequence.
To support our optimization and scale-up efforts, a versatile thermoregulated photoreactor was developed using Arduino and 3D-printing technologies.
Figure 1: XAT cross-coupling, difluoroamidation of indoles and pyrroles formation
Contact us to learn how our flow chemistry platform contributes to improve processes.
References
[1] P. Horáková, K. Kočí, Continuous-Flow Chemistry and Photochemistry for Manufacturing of Active
Pharmaceutical Ingredients Molecules 27 (2022) 8536–8565.
[2] A. Bogdan, M. Organ, Flow Chemistry as a Drug Discovery Tool: A Medicinal Chemistry Perspective
Flow Chemistry for the Synthesis of Heterocycles 56 (2018) 319–341.
[3] B. Quiclet-Sire, L. Quintero, G. Sanchez-Jimenez, S. Zard, A Practical Variation on the Paal-Knorr
Pyrrole Synthesis Synlett 01 (2003) 75–78.
[4] G. Yedase, A. Jha, V. Yatham, Visible-Light Enabled C(s p 3 )–C(s p 2 ) Cross-Electrophile Coupling
via Synergistic Halogen-Atom Transfer (XAT) and Nickel Catalysis J. Org. Chem. 87 (2022) 5442–
5450.