[en] 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(sp3 )-C(sp2 ) 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.
Disciplines :
Chemistry
Author, co-author :
Mazzarella, Daniele ; Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Pulcinella, Antonio ; Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Bovy, Loïc ; Université de Liège - ULiège > Département de chimie (sciences) > Synthèse organique appliquée ; Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Broersma, Rémy; Signify Research, High Tech Campus 7, 5656, AE, Eindhoven, The Netherlands
Noël, Timothy ; Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Language :
English
Title :
Rapid and Direct Photocatalytic C(sp3 )-H Acylation and Arylation in Flow.
A.P. and T.N. have received funding from the European Union H2020 research and innovation program under the Marie S. Curie Grant Agreement No 860762 (CHAIR). L.B. has received financial support from the European Union H2020 Erasmus+ program (OU201761).
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