---
_id: '14409'
abstract:
- lang: eng
text: We present a photon- and metal-free approach for the radical fluorination
of aliphatic oxalate-activated alcohols. The method relies on the spontaneous
generation of the N-(chloromethyl)triethylenediamine radical dication, a potent
single electron oxidant, from Selectfluor and 4-(dimethylamino)pyridine. The protocol
is easily scalable and provides the desired fluorinated products within only a
few minutes reaction time.
acknowledgement: We gratefully acknowledge the Max-Planck Society and the Institute
of Science and Technology Austria (ISTA) for generous financial support. We also
thank the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under
Germany's Excellence Strategy – EXC 2008 – 390540038 – UniSysCat for funding. B.P.
thanks the Boehringer Ingelheim Foundation for funding through the Plus 3 Perspectives
Programme.
article_number: e202300769
article_processing_charge: Yes (via OA deal)
article_type: original
author:
- first_name: Haralds
full_name: Baunis, Haralds
id: 2eea55ec-e8ec-11ed-86cb-d9c76787acfe
last_name: Baunis
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
citation:
ama: Baunis H, Pieber B. Formal radical deoxyfluorination of oxalate-activated alcohols
triggered by the selectfluor-DMAP charge-transfer complex. European Journal
of Organic Chemistry. 2023;26(42). doi:10.1002/ejoc.202300769
apa: Baunis, H., & Pieber, B. (2023). Formal radical deoxyfluorination of oxalate-activated
alcohols triggered by the selectfluor-DMAP charge-transfer complex. European
Journal of Organic Chemistry. Wiley. https://doi.org/10.1002/ejoc.202300769
chicago: Baunis, Haralds, and Bartholomäus Pieber. “Formal Radical Deoxyfluorination
of Oxalate-Activated Alcohols Triggered by the Selectfluor-DMAP Charge-Transfer
Complex.” European Journal of Organic Chemistry. Wiley, 2023. https://doi.org/10.1002/ejoc.202300769.
ieee: H. Baunis and B. Pieber, “Formal radical deoxyfluorination of oxalate-activated
alcohols triggered by the selectfluor-DMAP charge-transfer complex,” European
Journal of Organic Chemistry, vol. 26, no. 42. Wiley, 2023.
ista: Baunis H, Pieber B. 2023. Formal radical deoxyfluorination of oxalate-activated
alcohols triggered by the selectfluor-DMAP charge-transfer complex. European Journal
of Organic Chemistry. 26(42), e202300769.
mla: Baunis, Haralds, and Bartholomäus Pieber. “Formal Radical Deoxyfluorination
of Oxalate-Activated Alcohols Triggered by the Selectfluor-DMAP Charge-Transfer
Complex.” European Journal of Organic Chemistry, vol. 26, no. 42, e202300769,
Wiley, 2023, doi:10.1002/ejoc.202300769.
short: H. Baunis, B. Pieber, European Journal of Organic Chemistry 26 (2023).
date_created: 2023-10-08T22:01:18Z
date_published: 2023-11-07T00:00:00Z
date_updated: 2024-01-30T14:05:14Z
day: '07'
ddc:
- '540'
department:
- _id: BaPi
doi: 10.1002/ejoc.202300769
external_id:
isi:
- '001072666500001'
file:
- access_level: open_access
checksum: e8ad7865acd94672e476f273ccf3d542
content_type: application/pdf
creator: dernst
date_created: 2024-01-30T14:04:44Z
date_updated: 2024-01-30T14:04:44Z
file_id: '14913'
file_name: 2023_EurJOrgChem_Baunis.pdf
file_size: 3277622
relation: main_file
success: 1
file_date_updated: 2024-01-30T14:04:44Z
has_accepted_license: '1'
intvolume: ' 26'
isi: 1
issue: '42'
language:
- iso: eng
month: '11'
oa: 1
oa_version: Published Version
publication: European Journal of Organic Chemistry
publication_identifier:
eissn:
- 1099-0690
issn:
- 1434-193X
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Formal radical deoxyfluorination of oxalate-activated alcohols triggered by
the selectfluor-DMAP charge-transfer complex
tmp:
image: /images/cc_by_nc.png
legal_code_url: https://creativecommons.org/licenses/by-nc/4.0/legalcode
name: Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)
short: CC BY-NC (4.0)
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 26
year: '2023'
...
---
_id: '11969'
abstract:
- lang: eng
text: Photochemistry enables new synthetic means to form carbon–heteroatom bonds.
Photocatalysts can catalyze carbon–heteroatom cross-couplings by electron or energy
transfer either alone or in combination with a second catalyst. Photocatalyst-free
methods are possible using photolabile substrates or by generating photoactive
electron donor-acceptor complexes. This review summarizes and discusses the strategies
used in light-mediated carbon–heteroatom bond formations based on the proposed
mechanisms.
article_processing_charge: No
article_type: review
author:
- first_name: Cristian
full_name: Cavedon, Cristian
last_name: Cavedon
- first_name: Peter H.
full_name: Seeberger, Peter H.
last_name: Seeberger
- first_name: Bartholomäus
full_name: Pieber, Bartholomäus
id: 93e5e5b2-0da6-11ed-8a41-af589a024726
last_name: Pieber
orcid: 0000-0001-8689-388X
citation:
ama: Cavedon C, Seeberger PH, Pieber B. Photochemical strategies for carbon–heteroatom
bond formation. European Journal of Organic Chemistry. 2020;2020(10):1379-1392.
doi:10.1002/ejoc.201901173
apa: Cavedon, C., Seeberger, P. H., & Pieber, B. (2020). Photochemical strategies
for carbon–heteroatom bond formation. European Journal of Organic Chemistry.
Wiley. https://doi.org/10.1002/ejoc.201901173
chicago: Cavedon, Cristian, Peter H. Seeberger, and Bartholomäus Pieber. “Photochemical
Strategies for Carbon–Heteroatom Bond Formation.” European Journal of Organic
Chemistry. Wiley, 2020. https://doi.org/10.1002/ejoc.201901173.
ieee: C. Cavedon, P. H. Seeberger, and B. Pieber, “Photochemical strategies for
carbon–heteroatom bond formation,” European Journal of Organic Chemistry,
vol. 2020, no. 10. Wiley, pp. 1379–1392, 2020.
ista: Cavedon C, Seeberger PH, Pieber B. 2020. Photochemical strategies for carbon–heteroatom
bond formation. European Journal of Organic Chemistry. 2020(10), 1379–1392.
mla: Cavedon, Cristian, et al. “Photochemical Strategies for Carbon–Heteroatom Bond
Formation.” European Journal of Organic Chemistry, vol. 2020, no. 10, Wiley,
2020, pp. 1379–92, doi:10.1002/ejoc.201901173.
short: C. Cavedon, P.H. Seeberger, B. Pieber, European Journal of Organic Chemistry
2020 (2020) 1379–1392.
date_created: 2022-08-25T08:49:25Z
date_published: 2020-03-15T00:00:00Z
date_updated: 2023-02-21T10:09:47Z
day: '15'
doi: 10.1002/ejoc.201901173
extern: '1'
intvolume: ' 2020'
issue: '10'
language:
- iso: eng
main_file_link:
- open_access: '1'
url: https://doi.org/10.1002/ejoc.201901173
month: '03'
oa: 1
oa_version: Published Version
page: 1379-1392
publication: European Journal of Organic Chemistry
publication_identifier:
eissn:
- 1099-0690
issn:
- 1434-193X
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Photochemical strategies for carbon–heteroatom bond formation
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 2020
year: '2020'
...
---
_id: '12939'
abstract:
- lang: eng
text: 'Linear tetrapyrroles, called phyllobilins, are obtained as major catabolites
upon chlorophyll degradation. Primarily, colorless phylloleucobilins featuring
four deconjugated pyrrole units were identified. Their yellow counterparts, phylloxanthobilins,
were discovered more recently. Although the two catabolites differ only by one
double bond, physicochemical properties are very distinct. Moreover, the presence
of the double bond seems to enhance physiologically relevant bioactivities: in
contrast to phylloleucobilin, we identified a potent anti-proliferative activity
for a phylloxanthobilin, and show that this natural product induces apoptotic
cell death and a cell cycle arrest in cancer cells. Interestingly, upon modifying
inactive phylloleucobilin by esterification, an anti-proliferative activity can
be observed that increases with the chain lengths of the alkyl esters. We provide
first evidence for anti-cancer activity of phyllobilins, report a novel plant
source for a phylloxanthobilin, and by using paper spray MS, show that these bioactive
yellow chlorophyll catabolites are more prevalent in Nature than previously assumed.'
article_processing_charge: No
article_type: original
author:
- first_name: Cornelia A.
full_name: Karg, Cornelia A.
last_name: Karg
- first_name: Pengyu
full_name: Wang, Pengyu
last_name: Wang
- first_name: Florian
full_name: Kluibenschedl, Florian
id: 7499e70e-eb2c-11ec-b98b-f925648bc9d9
last_name: Kluibenschedl
- first_name: Thomas
full_name: Müller, Thomas
last_name: Müller
- first_name: Lars
full_name: Allmendinger, Lars
last_name: Allmendinger
- first_name: Angelika M.
full_name: Vollmar, Angelika M.
last_name: Vollmar
- first_name: Simone
full_name: Moser, Simone
last_name: Moser
citation:
ama: Karg CA, Wang P, Kluibenschedl F, et al. Phylloxanthobilins are abundant linear
tetrapyrroles from chlorophyll breakdown with activities against cancer cells.
European Journal of Organic Chemistry. 2020;2020(29):4499-4509. doi:10.1002/ejoc.202000692
apa: Karg, C. A., Wang, P., Kluibenschedl, F., Müller, T., Allmendinger, L., Vollmar,
A. M., & Moser, S. (2020). Phylloxanthobilins are abundant linear tetrapyrroles
from chlorophyll breakdown with activities against cancer cells. European Journal
of Organic Chemistry. Wiley. https://doi.org/10.1002/ejoc.202000692
chicago: Karg, Cornelia A., Pengyu Wang, Florian Kluibenschedl, Thomas Müller, Lars
Allmendinger, Angelika M. Vollmar, and Simone Moser. “Phylloxanthobilins Are Abundant
Linear Tetrapyrroles from Chlorophyll Breakdown with Activities against Cancer
Cells.” European Journal of Organic Chemistry. Wiley, 2020. https://doi.org/10.1002/ejoc.202000692.
ieee: C. A. Karg et al., “Phylloxanthobilins are abundant linear tetrapyrroles
from chlorophyll breakdown with activities against cancer cells,” European
Journal of Organic Chemistry, vol. 2020, no. 29. Wiley, pp. 4499–4509, 2020.
ista: Karg CA, Wang P, Kluibenschedl F, Müller T, Allmendinger L, Vollmar AM, Moser
S. 2020. Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll
breakdown with activities against cancer cells. European Journal of Organic Chemistry.
2020(29), 4499–4509.
mla: Karg, Cornelia A., et al. “Phylloxanthobilins Are Abundant Linear Tetrapyrroles
from Chlorophyll Breakdown with Activities against Cancer Cells.” European
Journal of Organic Chemistry, vol. 2020, no. 29, Wiley, 2020, pp. 4499–509,
doi:10.1002/ejoc.202000692.
short: C.A. Karg, P. Wang, F. Kluibenschedl, T. Müller, L. Allmendinger, A.M. Vollmar,
S. Moser, European Journal of Organic Chemistry 2020 (2020) 4499–4509.
date_created: 2023-05-10T14:49:30Z
date_published: 2020-08-09T00:00:00Z
date_updated: 2023-05-15T07:57:14Z
day: '09'
doi: 10.1002/ejoc.202000692
extern: '1'
intvolume: ' 2020'
issue: '29'
keyword:
- Organic Chemistry
- Physical and Theoretical Chemistry
language:
- iso: eng
main_file_link:
- open_access: '1'
url: https://doi.org/10.1002/ejoc.202000692
month: '08'
oa: 1
oa_version: Published Version
page: 4499-4509
publication: European Journal of Organic Chemistry
publication_identifier:
issn:
- 1434-193X
- 1099-0690
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown
with activities against cancer cells
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 2020
year: '2020'
...