Acridine-Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C-N Cross-Coupling.
Acridine
Catalysis
Covalent Organic Frameworks
C−N Cross-Coupling
Photoredox
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
16 May 2022
16 May 2022
Historique:
received:
28
12
2021
pubmed:
22
2
2022
medline:
22
2
2022
entrez:
21
2
2022
Statut:
ppublish
Résumé
Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF syntheses for broad applications, including heterogeneous catalysis. Herein, we report the synthesis of a new family of porous and crystalline COFs using a novel acridine linker and benzene-1,3,5-tricarbaldehyde derivatives bearing a variable number of hydroxy groups. With the broad absorption in the visible light region, the COFs were applied as photocatalysts in metallaphotocatalytic C-N cross-coupling. The fully β-ketoenamine linked COF showed the highest activity, due to the increased charge separation upon irradiation. The COF showed good to excellent yields for several aryl bromides, good recyclability and even catalyzed the organic transformation in presence of green light as energy source.
Identifiants
pubmed: 35188714
doi: 10.1002/anie.202117738
pmc: PMC9400916
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202117738Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : EXC 2008 - 390540038 - UniSysCat
Organisme : German Ministry of Education and Research (BMBF)
ID : PRODIGY (FKZ: 033RC024)
Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
J Am Chem Soc. 2018 Apr 25;140(16):5330-5333
pubmed: 29617560
J Am Chem Soc. 2018 Dec 5;140(48):16544-16552
pubmed: 30392360
Chem Soc Rev. 2020 Dec 7;49(23):8469-8500
pubmed: 33155009
Chem Soc Rev. 2020 Feb 10;49(3):708-735
pubmed: 31993598
Chem Rev. 2020 Aug 26;120(16):8814-8933
pubmed: 31967791
J Am Chem Soc. 2017 Feb 8;139(5):1856-1862
pubmed: 28106987
ACS Cent Sci. 2020 Jun 24;6(6):869-879
pubmed: 32607434
Angew Chem Int Ed Engl. 2016 Dec 12;55(50):15604-15608
pubmed: 27862737
J Am Chem Soc. 2014 Sep 3;136(35):12221-4
pubmed: 25046022
J Med Chem. 2016 May 26;59(10):4443-58
pubmed: 26571338
ACS Catal. 2019 Oct 4;9(10):9485-9498
pubmed: 35223139
Science. 2015 Sep 11;349(6253):1208-13
pubmed: 26292706
Chem Sci. 2019 Aug 5;10(36):8316-8322
pubmed: 31762969
J Chem Soc. 1948 Aug;10:1225-30
pubmed: 18884397
Science. 2016 Jul 15;353(6296):279-83
pubmed: 27338703
J Am Chem Soc. 2017 Aug 30;139(34):12035-12042
pubmed: 28829126
Chem Commun (Camb). 2019 Apr 18;55(33):4853-4856
pubmed: 30950459
Science. 2017 Mar 3;355(6328):
pubmed: 28254887
Angew Chem Int Ed Engl. 2022 May 16;61(21):e202117738
pubmed: 35188714
Chem Soc Rev. 2012 Sep 21;41(18):6010-22
pubmed: 22821129
J Am Chem Soc. 2021 Sep 29;143(38):15711-15722
pubmed: 34495671
J Am Chem Soc. 2008 Sep 3;130(35):11580-1
pubmed: 18683924
J Am Chem Soc. 2018 Jun 20;140(24):7667-7673
pubmed: 29787252
Chem Soc Rev. 2020 Jul 21;49(14):4637-4666
pubmed: 32597423
Angew Chem Int Ed Engl. 2019 Oct 14;58(42):14865-14870
pubmed: 31340082
Nat Commun. 2020 Oct 14;11(1):5179
pubmed: 33056986
Nat Chem. 2013 Jun;5(6):453-65
pubmed: 23695626
J Am Chem Soc. 2018 Apr 4;140(13):4623-4631
pubmed: 29584421
Angew Chem Int Ed Engl. 2012 Mar 26;51(13):3183-7
pubmed: 22334504
Chem Soc Rev. 2021 Jun 21;50(12):6871-6913
pubmed: 33881422
Angew Chem Int Ed Engl. 2020 May 11;59(20):7921-7927
pubmed: 32050048
Chem Soc Rev. 2013 Jan 21;42(2):548-68
pubmed: 23060270
J Am Chem Soc. 2020 Mar 11;142(10):4862-4871
pubmed: 32073853
ChemSusChem. 2017 Feb 22;10(4):664-669
pubmed: 28033455
Acc Chem Res. 2015 Dec 15;48(12):3053-63
pubmed: 26580002
Science. 2019 Jul 26;365(6451):360-366
pubmed: 31346061
Angew Chem Int Ed Engl. 2021 Aug 9;60(33):17810-17831
pubmed: 33252192
J Am Chem Soc. 2012 Dec 5;134(48):19524-7
pubmed: 23153356
J Am Chem Soc. 2019 Feb 6;141(5):1807-1822
pubmed: 30485740
Angew Chem Int Ed Engl. 2021 May 3;60(19):10820-10827
pubmed: 33538391