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Photoredox-Catalyzed Dehydrogenative Csp3–Csp2 Cross-Coupling of Alkylarenes to Aldehydes in Flow
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-09-15 , DOI: 10.1021/acs.joc.1c01621
Oliver M Griffiths 1 , Henrique A Esteves 1 , Yiding Chen 1 , Karin Sowa 1, 2 , Oliver S May 1 , Peter Morse 3 , David C Blakemore 3 , Steven V Ley 1
Affiliation  

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.

中文翻译:

光氧化还原催化脱氢 Csp3–Csp2 烷基芳烃与流动中的醛的交叉偶联

在流动中执行光氧化还原反应为经常遇到的有关重现性、反应时间和放大的问题提供了解决方案。在这里,我们报告了光氧化还原催化的烷基芳烃与醛的苄基偶联转移到流动化学设置,从而在更高的浓度、更短的停留时间、更好的产率、易于催化剂制备和增强的底物范围方面进行改进。其适用性已通过使用高功率发光二极管 (LED) 的多克级反应、选定活性药物成分 (API) 的后期功能化以及光催化剂回收方法得到证明。
更新日期:2021-10-01
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