Rapid and Direct Photocatalytic C(sp3 )-H Acylation and Arylation in Flow.

TBADT; acylation; arylation; flow chemistry; hydrogen atom transfer; Alkyl derivatives; Hydrogen atoms; Kinetic measurement; Nickel catalyst; Nucleophilic carbon; Overall process; Photo-catalytic; Reaction mechanism; Catalysis; Chemistry (all)

Abstract :

[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.

Publication date :

20 September 2021

Journal title :

Angewandte Chemie International Edition

ISSN :

1433-7851

eISSN :

1521-3773

Publisher :

John Wiley and Sons Inc, Germany

Volume :

Issue :

Pages :

21277 - 21282

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202108987

European Projects :

H2020 - 860762 - CHAIR - C-H Activation for Industrial Renewal

Funders :

EU - European Union

Funding text :

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).

Available on ORBi :

since 15 May 2024

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