Abstract
Executing photoredox reactions in flow offers solutions to frequently encountered issues regarding reproducibility, reaction time, and scale-up. Here, we report the transfer of a photoredox-catalyzed benzylic coupling of alkylarenes to aldehydes to a flow chemistry setting leading to improvements in terms of higher concentration, shorter residence times, better yields, ease of catalyst preparation, and enhanced substrate scope. Its applicability has been demonstrated by a multi-gram-scale reaction using high-power light-emitting diodes (LEDs), late-stage functionalization of selected active pharmaceutical ingredients (APIs), and also a photocatalyst recycling method.
Highlights
Constructing new Csp2−Csp3 bonds constitutes a significant process in the molecular assembly and late-stage functionalization of biologically relevant molecules
Noteworthy in this context, photoredox catalysis has arisen as a valuable tool that enables the construction of complex molecular architectures in a modular manner under mild conditions via the intermediacy of highly reactive species generated by various light sources
Despite the potential utility of this and related transformations, there are significant challenges hampering the widespread adoption of photochemical reactions more generally in chemical synthesis, in terms of scalability
Summary
Constructing new Csp2−Csp bonds constitutes a significant process in the molecular assembly and late-stage functionalization of biologically relevant molecules. The development of straightforward methods to quickly forge these bonds has been a focus of attention for synthetic chemists in recent years Noteworthy in this context, photoredox catalysis has arisen as a valuable tool that enables the construction of complex molecular architectures in a modular manner under mild conditions via the intermediacy of highly reactive species generated by various light sources.. Visible light-mediated reactions only take place on the periphery regions of a batch reaction vessel.8 To address these issues, many researchers have shown that transferring photochemical reactions to a continuous flow regime using high-power light-emitting diodes (LEDs) can improve reproducibility, scalability, reaction outcome, and reaction times..
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