---
_id: '12920'
abstract:
- lang: eng
text: The multicomponent approach allows to incorporate several functionalities
into a single covalent organic framework (COF) and consequently allows the construction
of bifunctional materials for cooperative catalysis. The well-defined structure
of such multicomponent COFs is furthermore ideally suited for structure-activity
relationship studies. We report a series of multicomponent COFs that contain acridine-
and 2,2’-bipyridine linkers connected through 1,3,5-benzenetrialdehyde derivatives.
The acridine motif is responsible for broad light absorption, while the bipyridine
unit enables complexation of nickel catalysts. These features enable the usage
of the framework materials as catalysts for light-mediated carbon−heteroatom cross-couplings.
Variation of the node units shows that the catalytic activity correlates to the
keto-enamine tautomer isomerism. This allows switching between high charge-carrier
mobility and persistent, localized charge-separated species depending on the nodes,
a tool to tailor the materials for specific reactions. Moreover, nickel-loaded
COFs are recyclable and catalyze cross-couplings even using red light irradiation.
article_number: e202202967
article_processing_charge: No
article_type: original
author:
- first_name: Michael
full_name: Traxler, Michael
last_name: Traxler
- first_name: Susanne
full_name: Reischauer, Susanne
last_name: Reischauer
- first_name: Sarah
full_name: Vogl, Sarah
last_name: Vogl
- first_name: Jérôme
full_name: Roeser, Jérôme
last_name: Roeser
- first_name: Jabor
full_name: Rabeah, Jabor
last_name: Rabeah
- first_name: Christopher
full_name: Penschke, Christopher
last_name: Penschke
- first_name: Peter
full_name: Saalfrank, Peter
last_name: Saalfrank
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
- first_name: Arne
full_name: Thomas, Arne
last_name: Thomas
citation:
ama: Traxler M, Reischauer S, Vogl S, et al. Programmable photocatalytic activity
of multicomponent covalent organic frameworks used as metallaphotocatalysts. Chemistry
– A European Journal. 2023;29(4). doi:10.1002/chem.202202967
apa: Traxler, M., Reischauer, S., Vogl, S., Roeser, J., Rabeah, J., Penschke, C.,
… Thomas, A. (2023). Programmable photocatalytic activity of multicomponent covalent
organic frameworks used as metallaphotocatalysts. Chemistry – A European Journal.
Wiley. https://doi.org/10.1002/chem.202202967
chicago: Traxler, Michael, Susanne Reischauer, Sarah Vogl, Jérôme Roeser, Jabor
Rabeah, Christopher Penschke, Peter Saalfrank, Bartholomäus Pieber, and Arne Thomas.
“Programmable Photocatalytic Activity of Multicomponent Covalent Organic Frameworks
Used as Metallaphotocatalysts.” Chemistry – A European Journal. Wiley,
2023. https://doi.org/10.1002/chem.202202967.
ieee: M. Traxler et al., “Programmable photocatalytic activity of multicomponent
covalent organic frameworks used as metallaphotocatalysts,” Chemistry – A European
Journal, vol. 29, no. 4. Wiley, 2023.
ista: Traxler M, Reischauer S, Vogl S, Roeser J, Rabeah J, Penschke C, Saalfrank
P, Pieber B, Thomas A. 2023. Programmable photocatalytic activity of multicomponent
covalent organic frameworks used as metallaphotocatalysts. Chemistry – A European
Journal. 29(4), e202202967.
mla: Traxler, Michael, et al. “Programmable Photocatalytic Activity of Multicomponent
Covalent Organic Frameworks Used as Metallaphotocatalysts.” Chemistry – A European
Journal, vol. 29, no. 4, e202202967, Wiley, 2023, doi:10.1002/chem.202202967.
short: M. Traxler, S. Reischauer, S. Vogl, J. Roeser, J. Rabeah, C. Penschke, P.
Saalfrank, B. Pieber, A. Thomas, Chemistry – A European Journal 29 (2023).
date_created: 2023-05-08T08:25:34Z
date_published: 2023-01-18T00:00:00Z
date_updated: 2023-05-15T08:39:24Z
day: '18'
doi: 10.1002/chem.202202967
extern: '1'
intvolume: ' 29'
issue: '4'
keyword:
- General Chemistry
- Catalysis
- Organic Chemistry
language:
- iso: eng
main_file_link:
- open_access: '1'
url: https://doi.org/10.1002/chem.202202967
month: '01'
oa: 1
oa_version: Published Version
publication: Chemistry – A European Journal
publication_identifier:
eissn:
- 1521-3765
issn:
- 0947-6539
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Programmable photocatalytic activity of multicomponent covalent organic frameworks
used as metallaphotocatalysts
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 29
year: '2023'
...
---
_id: '11962'
abstract:
- lang: eng
text: One of the rare alternative reagents for the reduction of carbon–carbon double
bonds is diimide (HNNH), which can be generated in situ from hydrazine hydrate
(N2H4⋅H2O) and O2. Although this selective method is extremely clean and powerful,
it is rarely used, as the rate-determining oxidation of hydrazine in the absence
of a catalyst is relatively slow using conventional batch protocols. A continuous
high-temperature/high-pressure methodology dramatically enhances the initial oxidation
step, at the same time allowing for a safe and scalable processing of the hazardous
reaction mixture. Simple alkenes can be selectively reduced within 10–20 min at
100–120 °C and 20 bar O2 pressure. The development of a multi-injection reactor
platform for the periodic addition of N2H4⋅H2O enables the reduction of less reactive
olefins even at lower reaction temperatures. This concept was utilized for the
highly selective reduction of artemisinic acid to dihydroartemisinic acid, the
precursor molecule for the semisynthesis of the antimalarial drug artemisinin.
The industrially relevant reduction was achieved by using four consecutive liquid
feeds (of N2H4⋅H2O) and residence time units resulting in a highly selective reduction
within approximately 40 min at 60 °C and 20 bar O2 pressure, providing dihydroartemisinic
acid in ≥93 % yield and ≥95 % selectivity.
article_processing_charge: No
article_type: original
author:
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
- first_name: Toma
full_name: Glasnov, Toma
last_name: Glasnov
- first_name: C. Oliver
full_name: Kappe, C. Oliver
last_name: Kappe
citation:
ama: Pieber B, Glasnov T, Kappe CO. Continuous flow reduction of artemisinic acid
utilizing multi-injection strategies-closing the gap towards a fully continuous
synthesis of antimalarial drugs. Chemistry - A European Journal. 2015;21(11):4368-4376.
doi:10.1002/chem.201406439
apa: Pieber, B., Glasnov, T., & Kappe, C. O. (2015). Continuous flow reduction
of artemisinic acid utilizing multi-injection strategies-closing the gap towards
a fully continuous synthesis of antimalarial drugs. Chemistry - A European
Journal. Wiley. https://doi.org/10.1002/chem.201406439
chicago: Pieber, Bartholomäus, Toma Glasnov, and C. Oliver Kappe. “Continuous Flow
Reduction of Artemisinic Acid Utilizing Multi-Injection Strategies-Closing the
Gap towards a Fully Continuous Synthesis of Antimalarial Drugs.” Chemistry
- A European Journal. Wiley, 2015. https://doi.org/10.1002/chem.201406439.
ieee: B. Pieber, T. Glasnov, and C. O. Kappe, “Continuous flow reduction of artemisinic
acid utilizing multi-injection strategies-closing the gap towards a fully continuous
synthesis of antimalarial drugs,” Chemistry - A European Journal, vol.
21, no. 11. Wiley, pp. 4368–4376, 2015.
ista: Pieber B, Glasnov T, Kappe CO. 2015. Continuous flow reduction of artemisinic
acid utilizing multi-injection strategies-closing the gap towards a fully continuous
synthesis of antimalarial drugs. Chemistry - A European Journal. 21(11), 4368–4376.
mla: Pieber, Bartholomäus, et al. “Continuous Flow Reduction of Artemisinic Acid
Utilizing Multi-Injection Strategies-Closing the Gap towards a Fully Continuous
Synthesis of Antimalarial Drugs.” Chemistry - A European Journal, vol.
21, no. 11, Wiley, 2015, pp. 4368–76, doi:10.1002/chem.201406439.
short: B. Pieber, T. Glasnov, C.O. Kappe, Chemistry - A European Journal 21 (2015)
4368–4376.
date_created: 2022-08-24T11:11:10Z
date_published: 2015-03-09T00:00:00Z
date_updated: 2023-02-21T10:09:30Z
day: '09'
doi: 10.1002/chem.201406439
extern: '1'
external_id:
pmid:
- '25655090'
intvolume: ' 21'
issue: '11'
language:
- iso: eng
month: '03'
oa_version: None
page: 4368-4376
pmid: 1
publication: Chemistry - A European Journal
publication_identifier:
eissn:
- 1521-3765
issn:
- 0947-6539
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Continuous flow reduction of artemisinic acid utilizing multi-injection strategies-closing
the gap towards a fully continuous synthesis of antimalarial drugs
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 21
year: '2015'
...
---
_id: '11963'
abstract:
- lang: eng
text: 'Peroxides and ethers in flow: 2-Carbonyl-substituted phenols and β-ketoesters
react safely with ethers in a microreactor environment using a copper catalyst
and an organic peroxide (TBHP). This protocol results in unsymmetrical acetal
scaffolds not easily available otherwise (see scheme).'
article_processing_charge: No
article_type: letter_note
author:
- first_name: G. Sathish
full_name: Kumar, G. Sathish
last_name: Kumar
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
- first_name: K. Rajender
full_name: Reddy, K. Rajender
last_name: Reddy
- first_name: C. Oliver
full_name: Kappe, C. Oliver
last_name: Kappe
citation:
ama: Kumar GS, Pieber B, Reddy KR, Kappe CO. Copper-catalyzed formation of C-O bonds
by direct α-C-H bond activation of ethers using stoichiometric amounts of peroxide
in batch and continuous-flow formats. Chemistry - A European Journal. 2012;18(20):6124-6128.
doi:10.1002/chem.201200815
apa: Kumar, G. S., Pieber, B., Reddy, K. R., & Kappe, C. O. (2012). Copper-catalyzed
formation of C-O bonds by direct α-C-H bond activation of ethers using stoichiometric
amounts of peroxide in batch and continuous-flow formats. Chemistry - A European
Journal. Wiley. https://doi.org/10.1002/chem.201200815
chicago: Kumar, G. Sathish, Bartholomäus Pieber, K. Rajender Reddy, and C. Oliver
Kappe. “Copper-Catalyzed Formation of C-O Bonds by Direct α-C-H Bond Activation
of Ethers Using Stoichiometric Amounts of Peroxide in Batch and Continuous-Flow
Formats.” Chemistry - A European Journal. Wiley, 2012. https://doi.org/10.1002/chem.201200815.
ieee: G. S. Kumar, B. Pieber, K. R. Reddy, and C. O. Kappe, “Copper-catalyzed formation
of C-O bonds by direct α-C-H bond activation of ethers using stoichiometric amounts
of peroxide in batch and continuous-flow formats,” Chemistry - A European Journal,
vol. 18, no. 20. Wiley, pp. 6124–6128, 2012.
ista: Kumar GS, Pieber B, Reddy KR, Kappe CO. 2012. Copper-catalyzed formation of
C-O bonds by direct α-C-H bond activation of ethers using stoichiometric amounts
of peroxide in batch and continuous-flow formats. Chemistry - A European Journal.
18(20), 6124–6128.
mla: Kumar, G. Sathish, et al. “Copper-Catalyzed Formation of C-O Bonds by Direct
α-C-H Bond Activation of Ethers Using Stoichiometric Amounts of Peroxide in Batch
and Continuous-Flow Formats.” Chemistry - A European Journal, vol. 18,
no. 20, Wiley, 2012, pp. 6124–28, doi:10.1002/chem.201200815.
short: G.S. Kumar, B. Pieber, K.R. Reddy, C.O. Kappe, Chemistry - A European Journal
18 (2012) 6124–6128.
date_created: 2022-08-24T12:33:05Z
date_published: 2012-05-14T00:00:00Z
date_updated: 2023-02-21T10:09:33Z
day: '14'
doi: 10.1002/chem.201200815
extern: '1'
external_id:
pmid:
- '22492535'
intvolume: ' 18'
issue: '20'
language:
- iso: eng
month: '05'
oa_version: None
page: 6124-6128
pmid: 1
publication: Chemistry - A European Journal
publication_identifier:
eissn:
- 1521-3765
issn:
- 0947-6539
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Copper-catalyzed formation of C-O bonds by direct α-C-H bond activation of
ethers using stoichiometric amounts of peroxide in batch and continuous-flow formats
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 18
year: '2012'
...
---
_id: '11964'
abstract:
- lang: eng
text: A detailed investigation on the direct arylation of benzene with aryl bromides
by using first-row transition metals under high-temperature/high-pressure (high-T/p)
conditions is described. By employing a parallel reactor platform for rapid reaction
screening and discovery at elevated temperatures, various metal/ligand/base combinations
were evaluated for their ability to enable biaryl formation through C-H activation.
The combination of cobalt(III) acetylacetonate and lithium bis(trimethylsilyl)amide
was subjected to further process intensification at 200 °C (15 bar), allowing
a significant reduction of the catalyst/base loading and a dramatic increase in
catalytic efficiency (turnover frequency) by a factor of 1000 compared to traditional
protocols. The high-throughput screening additionally identified novel nickel-
and copper-based metal/ligand combinations that favored an amination pathway competing
with C-H activation, with the addition of ligands, such as 1,10-phenanthroline,
having a profound influence on the selectivity. In addition to metal-based catalysts,
high-T/p process windows were also successfully applied to transition-metal-free
systems, utilizing 1,10-phenanthroline as organocatalyst.
article_processing_charge: No
article_type: original
author:
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
- first_name: David
full_name: Cantillo, David
last_name: Cantillo
- first_name: C. Oliver
full_name: Kappe, C. Oliver
last_name: Kappe
citation:
ama: 'Pieber B, Cantillo D, Kappe CO. Direct arylation of benzene with aryl bromides
using high‐temperature/high‐pressure process windows: Expanding the scope of C-H
activation chemistry. Chemistry – A European Journal. 2012;18(16):5047-5055.
doi:10.1002/chem.201103748'
apa: 'Pieber, B., Cantillo, D., & Kappe, C. O. (2012). Direct arylation of benzene
with aryl bromides using high‐temperature/high‐pressure process windows: Expanding
the scope of C-H activation chemistry. Chemistry – A European Journal.
Wiley. https://doi.org/10.1002/chem.201103748'
chicago: 'Pieber, Bartholomäus, David Cantillo, and C. Oliver Kappe. “Direct Arylation
of Benzene with Aryl Bromides Using High‐temperature/High‐pressure Process Windows:
Expanding the Scope of C-H Activation Chemistry.” Chemistry – A European Journal.
Wiley, 2012. https://doi.org/10.1002/chem.201103748.'
ieee: 'B. Pieber, D. Cantillo, and C. O. Kappe, “Direct arylation of benzene with
aryl bromides using high‐temperature/high‐pressure process windows: Expanding
the scope of C-H activation chemistry,” Chemistry – A European Journal,
vol. 18, no. 16. Wiley, pp. 5047–5055, 2012.'
ista: 'Pieber B, Cantillo D, Kappe CO. 2012. Direct arylation of benzene with aryl
bromides using high‐temperature/high‐pressure process windows: Expanding the scope
of C-H activation chemistry. Chemistry – A European Journal. 18(16), 5047–5055.'
mla: 'Pieber, Bartholomäus, et al. “Direct Arylation of Benzene with Aryl Bromides
Using High‐temperature/High‐pressure Process Windows: Expanding the Scope of C-H
Activation Chemistry.” Chemistry – A European Journal, vol. 18, no. 16,
Wiley, 2012, pp. 5047–55, doi:10.1002/chem.201103748.'
short: B. Pieber, D. Cantillo, C.O. Kappe, Chemistry – A European Journal 18 (2012)
5047–5055.
date_created: 2022-08-24T12:48:28Z
date_published: 2012-04-16T00:00:00Z
date_updated: 2023-02-21T10:09:35Z
day: '16'
doi: 10.1002/chem.201103748
extern: '1'
external_id:
pmid:
- '22396386'
intvolume: ' 18'
issue: '16'
language:
- iso: eng
month: '04'
oa_version: None
page: 5047-5055
pmid: 1
publication: Chemistry – A European Journal
publication_identifier:
eissn:
- 1521-3765
issn:
- 0947-6539
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: 'Direct arylation of benzene with aryl bromides using high‐temperature/high‐pressure
process windows: Expanding the scope of C-H activation chemistry'
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 18
year: '2012'
...