Literature DB >> 34329531

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

Daniele Mazzarella1, Antonio Pulcinella2, Loic Bovy3, Remy Broersma4, Timothy Noel5.   

Abstract

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.
© 2021 Wiley-VCH GmbH.

Entities:  

Keywords:  Acylation; TBADT; arylation; flow chemistry; hydrogen atom transfer

Year:  2021        PMID: 34329531     DOI: 10.1002/anie.202108987

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  11 in total

1.  Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides.

Authors:  Jingjing Zhang; Armido Studer
Journal:  Nat Commun       Date:  2022-07-06       Impact factor: 17.694

2.  Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis.

Authors:  Dingyi Wang; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

3.  Membrane-based TBADT recovery as a strategy to increase the sustainability of continuous-flow photocatalytic HAT transformations.

Authors:  Zhenghui Wen; Diego Pintossi; Manuel Nuño; Timothy Noël
Journal:  Nat Commun       Date:  2022-10-18       Impact factor: 17.694

Review 4.  Scale-Up of a Heterogeneous Photocatalytic Degradation Using a Photochemical Rotor-Stator Spinning Disk Reactor.

Authors:  Arnab Chaudhuri; Stefan D A Zondag; Jasper H A Schuurmans; John van der Schaaf; Timothy Noël
Journal:  Org Process Res Dev       Date:  2022-03-01       Impact factor: 3.858

Review 5.  Traditional and sustainable approaches for the construction of C-C bonds by harnessing C-H arylation.

Authors:  Jagrit Grover; Gaurav Prakash; Nupur Goswami; Debabrata Maiti
Journal:  Nat Commun       Date:  2022-02-28       Impact factor: 14.919

6.  Modular allylation of C(sp3)-H bonds by combining decatungstate photocatalysis and HWE olefination in flow.

Authors:  Luca Capaldo; Stefano Bonciolini; Antonio Pulcinella; Manuel Nuño; Timothy Noël
Journal:  Chem Sci       Date:  2022-05-31       Impact factor: 9.969

7.  C(sp3 )-H Arylation Promoted by a Heterogeneous Palladium-N-Heterocyclic Carbene Complex in Batch and Continuous Flow.

Authors:  Francesco Ferlin; Ioannis Anastasiou; Nihad Salameh; Takeru Miyakoshi; Olivier Baudoin; Luigi Vaccaro
Journal:  ChemSusChem       Date:  2022-02-18       Impact factor: 9.140

8.  Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis.

Authors:  Geun Seok Lee; Beomsoon Park; Soon Hyeok Hong
Journal:  Nat Commun       Date:  2022-09-03       Impact factor: 17.694

9.  The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins.

Authors:  Alberto Luridiana; Daniele Mazzarella; Luca Capaldo; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Manuel Nuño; Wybren Jan Buma; Timothy Noël
Journal:  ACS Catal       Date:  2022-09-01       Impact factor: 13.700

10.  Accelerated and Scalable C(sp3)-H Amination via Decatungstate Photocatalysis Using a Flow Photoreactor Equipped with High-Intensity LEDs.

Authors:  Ting Wan; Zhenghui Wen; Gabriele Laudadio; Luca Capaldo; Rob Lammers; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Rémy Broersma; Timothy Noël
Journal:  ACS Cent Sci       Date:  2021-12-16       Impact factor: 14.553

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