---
_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. <i>European Journal
    of Organic Chemistry</i>. 2023;26(42). doi:<a href="https://doi.org/10.1002/ejoc.202300769">10.1002/ejoc.202300769</a>
  apa: Baunis, H., &#38; Pieber, B. (2023). Formal radical deoxyfluorination of oxalate-activated
    alcohols triggered by the selectfluor-DMAP charge-transfer complex. <i>European
    Journal of Organic Chemistry</i>. Wiley. <a href="https://doi.org/10.1002/ejoc.202300769">https://doi.org/10.1002/ejoc.202300769</a>
  chicago: Baunis, Haralds, and Bartholomäus Pieber. “Formal Radical Deoxyfluorination
    of Oxalate-Activated Alcohols Triggered by the Selectfluor-DMAP Charge-Transfer
    Complex.” <i>European Journal of Organic Chemistry</i>. Wiley, 2023. <a href="https://doi.org/10.1002/ejoc.202300769">https://doi.org/10.1002/ejoc.202300769</a>.
  ieee: H. Baunis and B. Pieber, “Formal radical deoxyfluorination of oxalate-activated
    alcohols triggered by the selectfluor-DMAP charge-transfer complex,” <i>European
    Journal of Organic Chemistry</i>, 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.” <i>European Journal of Organic Chemistry</i>, vol. 26, no. 42, e202300769,
    Wiley, 2023, doi:<a href="https://doi.org/10.1002/ejoc.202300769">10.1002/ejoc.202300769</a>.
  short: H. Baunis, B. Pieber, European Journal of Organic Chemistry 26 (2023).
corr_author: '1'
date_created: 2023-10-08T22:01:18Z
date_published: 2023-11-07T00:00:00Z
date_updated: 2024-10-09T21:07:03Z
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. <i>European Journal of Organic Chemistry</i>. 2020;2020(10):1379-1392.
    doi:<a href="https://doi.org/10.1002/ejoc.201901173">10.1002/ejoc.201901173</a>
  apa: Cavedon, C., Seeberger, P. H., &#38; Pieber, B. (2020). Photochemical strategies
    for carbon–heteroatom bond formation. <i>European Journal of Organic Chemistry</i>.
    Wiley. <a href="https://doi.org/10.1002/ejoc.201901173">https://doi.org/10.1002/ejoc.201901173</a>
  chicago: Cavedon, Cristian, Peter H. Seeberger, and Bartholomäus Pieber. “Photochemical
    Strategies for Carbon–Heteroatom Bond Formation.” <i>European Journal of Organic
    Chemistry</i>. Wiley, 2020. <a href="https://doi.org/10.1002/ejoc.201901173">https://doi.org/10.1002/ejoc.201901173</a>.
  ieee: C. Cavedon, P. H. Seeberger, and B. Pieber, “Photochemical strategies for
    carbon–heteroatom bond formation,” <i>European Journal of Organic Chemistry</i>,
    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.” <i>European Journal of Organic Chemistry</i>, vol. 2020, no. 10, Wiley,
    2020, pp. 1379–92, doi:<a href="https://doi.org/10.1002/ejoc.201901173">10.1002/ejoc.201901173</a>.
  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: 2024-10-14T12:06:58Z
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'
...