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Rapid and Direct Photocatalytic C(sp 3 )−H Acylation and Arylation in Flow
Author(s) -
Mazzarella Daniele,
Pulcinella Antonio,
Bovy Loïc,
Broersma Rémy,
Noël Timothy
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202108987
Subject(s) - photocatalysis , acylation , chemistry , nucleophile , catalysis , radical , photochemistry , carbon fibers , alkyl , flow chemistry , hydrogen atom , hydrogen bond , nickel , hydrogen , medicinal chemistry , organic chemistry , molecule , materials science , composite number , composite material
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.