---
OA_place: publisher
OA_type: hybrid
PlanS_conform: '1'
_id: '21776'
abstract:
- lang: eng
  text: Pyridyl motifs equipped with N-substituents can be powerful ligands for catalysis,
    yet their broader adoption is limited by the lack of a practical method to prepare
    these scaffolds. We report a modular, robust, and versatile Buchwald–Hartwig amination
    protocol that enables the rapid synthesis of bipyridine, phenanthroline, terpyridine,
    and pybox ligands bearing dialkylamine, diarylamine, and heteroaromatic N-substituents.
    These conditions streamline ligand library synthesis and will facilitate systematic
    studies in catalysis and related applications.
acknowledged_ssus:
- _id: LifeSc
- _id: MassSpec
- _id: NMR
- _id: M-Shop
acknowledgement: We gratefully acknowledge ISTA for generous financial support. B.P.
  acknowledges the Austrian Science Fund (PAT 1250924) and the ACS GCI Pharmaceutical
  Roundtable for funding; T.P.Y acknowledges the NSF(CHE-2349003) for financial support.
  This research was supported by the Scientific Service Units (SSU) of ISTA through
  resources provided by the Lab Support Facility, Mass Spec Facility, NMR facility,
  and the Miba Machine Shop. We specifically thank Aikaterina Paraskevopoulou for
  HRMS measurements and Jan Pecak for support with ICP-OES experi-ments. NMR facilities
  at UW−Madison were supported by the NSF(CHE-1048642) and a generous gift from Paul
  J. and Margaret M. Bender. Open Access funding provided by Institute of Science
  and Technology Austria/KEMÖ. This study was supported by Austrian Science Fund (PAT
  1250924), ACSGCI Pharmaceutical Roundtable, and National Science Foundation(CHE-2349003)
  and (CHE-1048642).
article_number: e70417
article_processing_charge: Yes (via OA deal)
article_type: original
author:
- first_name: Adam
  full_name: Petrik, Adam
  id: e273d403-329f-11ee-a353-8c34c056f8ed
  last_name: Petrik
- first_name: Aleksander
  full_name: Bena, Aleksander
  id: 4197c39e-e8ec-11ed-86cb-afed934cd664
  last_name: Bena
- first_name: Haralds
  full_name: Baunis, Haralds
  id: 2eea55ec-e8ec-11ed-86cb-d9c76787acfe
  last_name: Baunis
- first_name: Riley M.
  full_name: Kelch, Riley M.
  last_name: Kelch
- first_name: Tehshik P.
  full_name: Yoon, Tehshik P.
  last_name: Yoon
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Petrik A, Bena A, Baunis H, Kelch RM, Yoon TP, Pieber B. Facile access to N-substituted
    pyridyl ligands. <i>Advanced Synthesis &#38; Catalysis</i>. 2026;368(9). doi:<a
    href="https://doi.org/10.1002/adsc.70417">10.1002/adsc.70417</a>
  apa: Petrik, A., Bena, A., Baunis, H., Kelch, R. M., Yoon, T. P., &#38; Pieber,
    B. (2026). Facile access to N-substituted pyridyl ligands. <i>Advanced Synthesis
    &#38; Catalysis</i>. Wiley. <a href="https://doi.org/10.1002/adsc.70417">https://doi.org/10.1002/adsc.70417</a>
  chicago: Petrik, Adam, Aleksander Bena, Haralds Baunis, Riley M. Kelch, Tehshik
    P. Yoon, and Bartholomäus Pieber. “Facile Access to N-Substituted Pyridyl Ligands.”
    <i>Advanced Synthesis &#38; Catalysis</i>. Wiley, 2026. <a href="https://doi.org/10.1002/adsc.70417">https://doi.org/10.1002/adsc.70417</a>.
  ieee: A. Petrik, A. Bena, H. Baunis, R. M. Kelch, T. P. Yoon, and B. Pieber, “Facile
    access to N-substituted pyridyl ligands,” <i>Advanced Synthesis &#38; Catalysis</i>,
    vol. 368, no. 9. Wiley, 2026.
  ista: Petrik A, Bena A, Baunis H, Kelch RM, Yoon TP, Pieber B. 2026. Facile access
    to N-substituted pyridyl ligands. Advanced Synthesis &#38; Catalysis. 368(9),
    e70417.
  mla: Petrik, Adam, et al. “Facile Access to N-Substituted Pyridyl Ligands.” <i>Advanced
    Synthesis &#38; Catalysis</i>, vol. 368, no. 9, e70417, Wiley, 2026, doi:<a href="https://doi.org/10.1002/adsc.70417">10.1002/adsc.70417</a>.
  short: A. Petrik, A. Bena, H. Baunis, R.M. Kelch, T.P. Yoon, B. Pieber, Advanced
    Synthesis &#38; Catalysis 368 (2026).
corr_author: '1'
date_created: 2026-05-03T22:01:36Z
date_published: 2026-05-05T00:00:00Z
date_updated: 2026-05-07T07:33:33Z
day: '05'
ddc:
- '540'
department:
- _id: BaPi
- _id: GradSch
doi: 10.1002/adsc.70417
file:
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  content_type: application/pdf
  creator: dernst
  date_created: 2026-05-07T07:29:24Z
  date_updated: 2026-05-07T07:29:24Z
  file_id: '21833'
  file_name: 2026_AdvSynthCatal_Petrik.pdf
  file_size: 437184
  relation: main_file
  success: 1
file_date_updated: 2026-05-07T07:29:24Z
fulldoi: https://doi.org/10.1002/adsc.70417
has_accepted_license: '1'
intvolume: '       368'
issue: '9'
language:
- iso: eng
license: https://creativecommons.org/licenses/by/4.0/
month: '05'
oa: 1
oa_version: Published Version
project:
- _id: 8f1d607d-16d5-11f0-9cad-ab453295ba5e
  grant_number: PAT 1250924
  name: Photoactive ligands for transformative nickel catalysis
publication: Advanced Synthesis & Catalysis
publication_identifier:
  eissn:
  - 1615-4169
  issn:
  - 1615-4150
publication_status: published
publisher: Wiley
quality_controlled: '1'
scopus_import: '1'
status: public
title: Facile access to N-substituted pyridyl ligands
tmp:
  image: /images/cc_by.png
  legal_code_url: https://creativecommons.org/licenses/by/4.0/legalcode
  name: Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)
  short: CC BY (4.0)
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 368
year: '2026'
...
---
OA_place: publisher
OA_type: hybrid
PlanS_conform: '1'
_id: '19599'
abstract:
- lang: eng
  text: Advances in nickel catalysis have significantly broadened the synthetic chemists’
    toolbox, particularly through methodologies leveraging paramagnetic nickel species
    via photoredox catalysis or electrochemistry. Key to these reactions is the oxidation
    state modulation of nickel via single-electron transfer events. Recent mechanistic
    studies indicate that C(sp2)–heteroatom bond formations proceed through NiI/NiIII
    cycles. Related C(sp2)–C(sp3) cross-couplings operate via the photocatalytic generation
    of C-centered radicals and a catalytic cycle that involves Ni0, NiI, and NiIII
    species. Here, we show that light-mediated nickel-catalyzed C(sp2)–C(sp3) bond
    formations can be carried out without using exogenous photoredox catalysts but
    with a photoactive ligand. In a pursuit of expanding the scope of C(sp2)–heteroatom
    couplings using donor–acceptor ligands, we identified a photoactive nickel complex
    capable of catalyzing cross-couplings between aryl halides and benzyltrifluoroborate
    salts. Mechanistic investigations provide evidence that transmetalation between
    a photochemically generated NiI species and the organoboron compound is the key
    catalytic step in a NiI/NiIII catalytic cycle under these conditions.
acknowledged_ssus:
- _id: LifeSc
- _id: NMR
acknowledgement: This research was supported by the Scientific Service Units (SSU)
  of ISTA through resources provided by the Lab Support Facility (LSF), Mass Spec
  Facility, and NMR Facility. We gratefully acknowledge the Institute of Science and
  Technology Austria (ISTA) and the Max-Planck Society for their generous financial
  support. R.M.v.d.V. and B.P. thank the Deutsche Forschungsgemeinschaft (DFG, German
  Research Foundation) under Germany’s Excellence Strategy – EXC 2008 – 390540038
  – UniSysCat for funding. B.P. thanks the DFG (PI 1635/2-19), the Boehringer Ingelheim
  Foundation (Plus 3 Perspectives Programme), and the FWF (Austrian Science Fund;
  PAT 1250924) for financial support. J.H.B. acknowledges the Robert C. and Carolyn
  J. Springborn Endowment for Student Support Program at the University of Illinois
  Urbana–Champaign. R.F.W. was supported by a fellowship from the Deutscher Akademischer
  Austauschdienst (DAAD). We thank Dr. John J. Molloy (MPICI) for scientific discussions.
article_processing_charge: Yes (via OA deal)
article_type: original
author:
- first_name: Lucia
  full_name: Anghileri, Lucia
  id: 7b65e46e-1f51-11f0-8ea0-faa153157f5e
  last_name: Anghileri
- first_name: Haralds
  full_name: Baunis, Haralds
  id: 2eea55ec-e8ec-11ed-86cb-d9c76787acfe
  last_name: Baunis
- first_name: Aleksander
  full_name: Bena, Aleksander
  id: 4197c39e-e8ec-11ed-86cb-afed934cd664
  last_name: Bena
- first_name: Christos
  full_name: Giannoudis, Christos
  id: 1bd506c6-e8ec-11ed-86cb-d495f63f2dcd
  last_name: Giannoudis
- first_name: John H.
  full_name: Burke, John H.
  last_name: Burke
- first_name: Susanne
  full_name: Reischauer, Susanne
  last_name: Reischauer
- first_name: Christoph
  full_name: Merschjann, Christoph
  last_name: Merschjann
- first_name: Rachel F.
  full_name: Wallick, Rachel F.
  last_name: Wallick
- first_name: Tarek
  full_name: Al Said, Tarek
  last_name: Al Said
- first_name: Callum E
  full_name: Adams, Callum E
  id: 126d6d0f-fdc1-11ee-bb4a-9f462709fa9d
  last_name: Adams
- first_name: Gianluca
  full_name: Simionato, Gianluca
  last_name: Simionato
- first_name: Sergey
  full_name: Kovalenko, Sergey
  last_name: Kovalenko
- first_name: Luca
  full_name: Dell’Amico, Luca
  last_name: Dell’Amico
- first_name: Renske M.
  full_name: Van Der Veen, Renske M.
  last_name: Van Der Veen
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Anghileri L, Baunis H, Bena A, et al. Evidence for a unifying NiI/NiIII mechanism
    in light-mediated cross-coupling catalysis. <i>Journal of the American Chemical
    Society</i>. 2025;147(16):13169–13179. doi:<a href="https://doi.org/10.1021/jacs.4c16050">10.1021/jacs.4c16050</a>
  apa: Anghileri, L., Baunis, H., Bena, A., Giannoudis, C., Burke, J. H., Reischauer,
    S., … Pieber, B. (2025). Evidence for a unifying NiI/NiIII mechanism in light-mediated
    cross-coupling catalysis. <i>Journal of the American Chemical Society</i>. American
    Chemical Society. <a href="https://doi.org/10.1021/jacs.4c16050">https://doi.org/10.1021/jacs.4c16050</a>
  chicago: Anghileri, Lucia, Haralds Baunis, Aleksander Bena, Christos Giannoudis,
    John H. Burke, Susanne Reischauer, Christoph Merschjann, et al. “Evidence for
    a Unifying NiI/NiIII Mechanism in Light-Mediated Cross-Coupling Catalysis.” <i>Journal
    of the American Chemical Society</i>. American Chemical Society, 2025. <a href="https://doi.org/10.1021/jacs.4c16050">https://doi.org/10.1021/jacs.4c16050</a>.
  ieee: L. Anghileri <i>et al.</i>, “Evidence for a unifying NiI/NiIII mechanism in
    light-mediated cross-coupling catalysis,” <i>Journal of the American Chemical
    Society</i>, vol. 147, no. 16. American Chemical Society, pp. 13169–13179, 2025.
  ista: Anghileri L, Baunis H, Bena A, Giannoudis C, Burke JH, Reischauer S, Merschjann
    C, Wallick RF, Al Said T, Adams CE, Simionato G, Kovalenko S, Dell’Amico L, Van
    Der Veen RM, Pieber B. 2025. Evidence for a unifying NiI/NiIII mechanism in light-mediated
    cross-coupling catalysis. Journal of the American Chemical Society. 147(16), 13169–13179.
  mla: Anghileri, Lucia, et al. “Evidence for a Unifying NiI/NiIII Mechanism in Light-Mediated
    Cross-Coupling Catalysis.” <i>Journal of the American Chemical Society</i>, vol.
    147, no. 16, American Chemical Society, 2025, pp. 13169–13179, doi:<a href="https://doi.org/10.1021/jacs.4c16050">10.1021/jacs.4c16050</a>.
  short: L. Anghileri, H. Baunis, A. Bena, C. Giannoudis, J.H. Burke, S. Reischauer,
    C. Merschjann, R.F. Wallick, T. Al Said, C.E. Adams, G. Simionato, S. Kovalenko,
    L. Dell’Amico, R.M. Van Der Veen, B. Pieber, Journal of the American Chemical
    Society 147 (2025) 13169–13179.
corr_author: '1'
date_created: 2025-04-20T22:01:28Z
date_published: 2025-04-11T00:00:00Z
date_updated: 2025-10-02T08:22:12Z
day: '11'
ddc:
- '540'
department:
- _id: BaPi
doi: 10.1021/jacs.4c16050
external_id:
  isi:
  - '001465858000001'
  pmid:
  - '40211781'
file:
- access_level: open_access
  checksum: 7f2b6a3c23b062490f37cce10ced46aa
  content_type: application/pdf
  creator: dernst
  date_created: 2025-08-05T13:04:42Z
  date_updated: 2025-08-05T13:04:42Z
  file_id: '20137'
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  relation: main_file
  success: 1
file_date_updated: 2025-08-05T13:04:42Z
fulldoi: https://doi.org/10.1021/jacs.4c16050
has_accepted_license: '1'
intvolume: '       147'
isi: 1
issue: '16'
language:
- iso: eng
month: '04'
oa: 1
oa_version: Published Version
page: 13169–13179
pmid: 1
project:
- _id: 8f1d607d-16d5-11f0-9cad-ab453295ba5e
  grant_number: PAT 1250924
  name: Photoactive ligands for transformative nickel catalysis
publication: Journal of the American Chemical Society
publication_identifier:
  eissn:
  - 1520-5126
  issn:
  - 0002-7863
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Evidence for a unifying NiI/NiIII mechanism in light-mediated cross-coupling
  catalysis
tmp:
  image: /images/cc_by.png
  legal_code_url: https://creativecommons.org/licenses/by/4.0/legalcode
  name: Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)
  short: CC BY (4.0)
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 147
year: '2025'
...
---
_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
fulldoi: https://doi.org/10.1002/ejoc.202300769
has_accepted_license: '1'
intvolume: '        26'
isi: 1
issue: '42'
language:
- iso: eng
license: https://creativecommons.org/licenses/by-nc/4.0/
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'
...