[{"doi":"10.1002/adsc.70417","article_type":"original","PlanS_conform":"1","oa_version":"Published Version","ddc":["540"],"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"}],"title":"Facile access to N-substituted pyridyl ligands","department":[{"_id":"BaPi"},{"_id":"GradSch"}],"OA_type":"hybrid","quality_controlled":"1","corr_author":"1","day":"05","date_created":"2026-05-03T22:01:36Z","author":[{"last_name":"Petrik","first_name":"Adam","id":"e273d403-329f-11ee-a353-8c34c056f8ed","full_name":"Petrik, Adam"},{"id":"4197c39e-e8ec-11ed-86cb-afed934cd664","full_name":"Bena, Aleksander","first_name":"Aleksander","last_name":"Bena"},{"first_name":"Haralds","full_name":"Baunis, Haralds","id":"2eea55ec-e8ec-11ed-86cb-d9c76787acfe","last_name":"Baunis"},{"last_name":"Kelch","full_name":"Kelch, Riley M.","first_name":"Riley M."},{"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"}],"OA_place":"publisher","license":"https://creativecommons.org/licenses/by/4.0/","project":[{"_id":"8f1d607d-16d5-11f0-9cad-ab453295ba5e","grant_number":"PAT 1250924","name":"Photoactive ligands for transformative nickel catalysis"}],"intvolume":"       368","type":"journal_article","date_updated":"2026-05-07T07:33:33Z","article_number":"e70417","publication_status":"published","status":"public","publication_identifier":{"issn":["1615-4150"],"eissn":["1615-4169"]},"issue":"9","publisher":"Wiley","month":"05","year":"2026","tmp":{"name":"Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)","legal_code_url":"https://creativecommons.org/licenses/by/4.0/legalcode","short":"CC BY (4.0)","image":"/images/cc_by.png"},"publication":"Advanced Synthesis & Catalysis","_id":"21776","article_processing_charge":"Yes (via OA deal)","citation":{"short":"A. Petrik, A. Bena, H. Baunis, R.M. Kelch, T.P. Yoon, B. Pieber, Advanced Synthesis &#38; Catalysis 368 (2026).","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>","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>","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.","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>.","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>.","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."},"volume":368,"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).","file_date_updated":"2026-05-07T07:29:24Z","has_accepted_license":"1","oa":1,"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","file":[{"date_created":"2026-05-07T07:29:24Z","relation":"main_file","checksum":"afe9752977898642c903abdc70b4a283","success":1,"content_type":"application/pdf","access_level":"open_access","file_name":"2026_AdvSynthCatal_Petrik.pdf","file_size":437184,"creator":"dernst","file_id":"21833","date_updated":"2026-05-07T07:29:24Z"}],"language":[{"iso":"eng"}],"fulldoi":"https://doi.org/10.1002/adsc.70417","scopus_import":"1","date_published":"2026-05-05T00:00:00Z"},{"article_type":"original","doi":"10.1021/jacs.4c16050","ddc":["540"],"oa_version":"Published Version","PlanS_conform":"1","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"}],"department":[{"_id":"BaPi"}],"title":"Evidence for a unifying NiI/NiIII mechanism in light-mediated cross-coupling catalysis","OA_type":"hybrid","quality_controlled":"1","page":"13169–13179","corr_author":"1","day":"11","isi":1,"date_created":"2025-04-20T22:01:28Z","OA_place":"publisher","author":[{"first_name":"Lucia","full_name":"Anghileri, Lucia","id":"7b65e46e-1f51-11f0-8ea0-faa153157f5e","last_name":"Anghileri"},{"last_name":"Baunis","full_name":"Baunis, Haralds","id":"2eea55ec-e8ec-11ed-86cb-d9c76787acfe","first_name":"Haralds"},{"full_name":"Bena, Aleksander","id":"4197c39e-e8ec-11ed-86cb-afed934cd664","first_name":"Aleksander","last_name":"Bena"},{"last_name":"Giannoudis","first_name":"Christos","id":"1bd506c6-e8ec-11ed-86cb-d495f63f2dcd","full_name":"Giannoudis, Christos"},{"last_name":"Burke","full_name":"Burke, John H.","first_name":"John H."},{"full_name":"Reischauer, Susanne","first_name":"Susanne","last_name":"Reischauer"},{"last_name":"Merschjann","full_name":"Merschjann, Christoph","first_name":"Christoph"},{"first_name":"Rachel F.","full_name":"Wallick, Rachel F.","last_name":"Wallick"},{"first_name":"Tarek","full_name":"Al Said, Tarek","last_name":"Al Said"},{"id":"126d6d0f-fdc1-11ee-bb4a-9f462709fa9d","full_name":"Adams, Callum E","first_name":"Callum E","last_name":"Adams"},{"first_name":"Gianluca","full_name":"Simionato, Gianluca","last_name":"Simionato"},{"full_name":"Kovalenko, Sergey","first_name":"Sergey","last_name":"Kovalenko"},{"first_name":"Luca","full_name":"Dell’Amico, Luca","last_name":"Dell’Amico"},{"last_name":"Van Der Veen","full_name":"Van Der Veen, Renske M.","first_name":"Renske M."},{"orcid":"0000-0001-8689-388X","last_name":"Pieber","first_name":"Bartholomäus","full_name":"Pieber, Bartholomäus","id":"93e5e5b2-0da6-11ed-8a41-af589a024726"}],"project":[{"grant_number":"PAT 1250924","_id":"8f1d607d-16d5-11f0-9cad-ab453295ba5e","name":"Photoactive ligands for transformative nickel catalysis"}],"intvolume":"       147","type":"journal_article","pmid":1,"date_updated":"2025-10-02T08:22:12Z","publication_status":"published","status":"public","publication_identifier":{"eissn":["1520-5126"],"issn":["0002-7863"]},"issue":"16","publisher":"American Chemical Society","month":"04","tmp":{"name":"Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)","legal_code_url":"https://creativecommons.org/licenses/by/4.0/legalcode","short":"CC BY (4.0)","image":"/images/cc_by.png"},"year":"2025","publication":"Journal of the American Chemical Society","_id":"19599","volume":147,"citation":{"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.","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>.","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>.","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>","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.","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.","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>"},"article_processing_charge":"Yes (via OA deal)","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.","external_id":{"isi":["001465858000001"],"pmid":["40211781"]},"file_date_updated":"2025-08-05T13:04:42Z","has_accepted_license":"1","oa":1,"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","file":[{"checksum":"7f2b6a3c23b062490f37cce10ced46aa","success":1,"relation":"main_file","date_created":"2025-08-05T13:04:42Z","file_id":"20137","date_updated":"2025-08-05T13:04:42Z","creator":"dernst","file_size":4179314,"file_name":"2025_JACS_Anghileri.pdf","access_level":"open_access","content_type":"application/pdf"}],"fulldoi":"https://doi.org/10.1021/jacs.4c16050","scopus_import":"1","language":[{"iso":"eng"}],"date_published":"2025-04-11T00:00:00Z"},{"publication":"European Journal of Organic Chemistry","_id":"14409","month":"11","publisher":"Wiley","tmp":{"image":"/images/cc_by_nc.png","legal_code_url":"https://creativecommons.org/licenses/by-nc/4.0/legalcode","short":"CC BY-NC (4.0)","name":"Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)"},"year":"2023","file":[{"file_id":"14913","date_updated":"2024-01-30T14:04:44Z","file_name":"2023_EurJOrgChem_Baunis.pdf","file_size":3277622,"creator":"dernst","access_level":"open_access","content_type":"application/pdf","checksum":"e8ad7865acd94672e476f273ccf3d542","success":1,"relation":"main_file","date_created":"2024-01-30T14:04:44Z"}],"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","scopus_import":"1","fulldoi":"https://doi.org/10.1002/ejoc.202300769","language":[{"iso":"eng"}],"date_published":"2023-11-07T00:00:00Z","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.","volume":26,"citation":{"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.","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>.","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>.","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>","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.","short":"H. Baunis, B. Pieber, European Journal of Organic Chemistry 26 (2023).","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>"},"article_processing_charge":"Yes (via OA deal)","has_accepted_license":"1","oa":1,"file_date_updated":"2024-01-30T14:04:44Z","external_id":{"isi":["001072666500001"]},"date_updated":"2024-10-09T21:07:03Z","publication_identifier":{"issn":["1434-193X"],"eissn":["1099-0690"]},"issue":"42","publication_status":"published","article_number":"e202300769","status":"public","corr_author":"1","day":"07","license":"https://creativecommons.org/licenses/by-nc/4.0/","author":[{"last_name":"Baunis","id":"2eea55ec-e8ec-11ed-86cb-d9c76787acfe","full_name":"Baunis, Haralds","first_name":"Haralds"},{"id":"93e5e5b2-0da6-11ed-8a41-af589a024726","full_name":"Pieber, Bartholomäus","first_name":"Bartholomäus","orcid":"0000-0001-8689-388X","last_name":"Pieber"}],"intvolume":"        26","type":"journal_article","date_created":"2023-10-08T22:01:18Z","isi":1,"ddc":["540"],"oa_version":"Published Version","doi":"10.1002/ejoc.202300769","article_type":"original","quality_controlled":"1","abstract":[{"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.","lang":"eng"}],"department":[{"_id":"BaPi"}],"title":"Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex"}]