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Rapid and Direct Photocatalytic C(sp^3^)−H Acylation and Arylation in Flow by Daniele Mazzarella; Antonio Pulcinella; Loïc Bovy; Rémy Broersma; Timothy Noël is a Chemistry article available to read on EtoBox.

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Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp 3 )-C(sp 2 ) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12-48 hours to only 5-15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process. The advent of photoredox catalysis [1] has not only renewed the interest of the synthetic community into radical chemistry, [2] but also stimulated the development of kindred branches such as metallaphotoredox catalysis. [3] In this field, the radical, generated by photocatalytic means, is intercepted by a transition metal catalyst and enables the construction of carbon-carbon and carbon-heteroatom bonds. While several examples take advantage of the combination of functionalized substrates and matched redox photocatalytic properties (via single electron transfer,

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Author

Daniele Mazzarella; Antonio Pulcinella; Loïc Bovy; Rémy Broersma; Timothy Noël

Publisher

Wiley

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)