Photoredox-Catalyzed Dehydrogenative Csp3–Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-10, Vol.86 (19), p.13559-13571
Main Authors: Griffiths, Oliver M, Esteves, Henrique A, Chen, Yiding, Sowa, Karin, May, Oliver S, Morse, Peter, Blakemore, David C, Ley, Steven V
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01621