[{"author":[{"full_name":"Baunis, Haralds","first_name":"Haralds","last_name":"Baunis","id":"2eea55ec-e8ec-11ed-86cb-d9c76787acfe"},{"first_name":"Bartholomäus","last_name":"Pieber","orcid":"0000-0001-8689-388X","full_name":"Pieber, Bartholomäus","id":"93e5e5b2-0da6-11ed-8a41-af589a024726"}],"issue":"42","_id":"14409","scopus_import":"1","title":"Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex","intvolume":"        26","publication_status":"published","article_processing_charge":"Yes (via OA deal)","department":[{"_id":"BaPi"}],"date_created":"2023-10-08T22:01:18Z","file_date_updated":"2024-01-30T14:04:44Z","quality_controlled":"1","article_type":"original","publisher":"Wiley","isi":1,"external_id":{"isi":["001072666500001"]},"date_updated":"2024-01-30T14:05:14Z","citation":{"short":"H. Baunis, B. Pieber, European Journal of Organic Chemistry 26 (2023).","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>.","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.","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."},"year":"2023","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"}],"doi":"10.1002/ejoc.202300769","day":"07","ddc":["540"],"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,"publication":"European Journal of Organic Chemistry","has_accepted_license":"1","month":"11","article_number":"e202300769","oa_version":"Published Version","language":[{"iso":"eng"}],"date_published":"2023-11-07T00:00:00Z","type":"journal_article","tmp":{"name":"Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)","image":"/images/cc_by_nc.png","short":"CC BY-NC (4.0)","legal_code_url":"https://creativecommons.org/licenses/by-nc/4.0/legalcode"},"oa":1,"publication_identifier":{"issn":["1434-193X"],"eissn":["1099-0690"]},"status":"public","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","file":[{"file_size":3277622,"checksum":"e8ad7865acd94672e476f273ccf3d542","date_created":"2024-01-30T14:04:44Z","content_type":"application/pdf","file_name":"2023_EurJOrgChem_Baunis.pdf","date_updated":"2024-01-30T14:04:44Z","relation":"main_file","success":1,"access_level":"open_access","creator":"dernst","file_id":"14913"}]},{"language":[{"iso":"eng"}],"oa_version":"Published Version","month":"03","publication":"European Journal of Organic Chemistry","main_file_link":[{"url":"https://doi.org/10.1002/ejoc.201901173","open_access":"1"}],"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","status":"public","publication_identifier":{"issn":["1434-193X"],"eissn":["1099-0690"]},"oa":1,"date_published":"2020-03-15T00:00:00Z","type":"journal_article","publisher":"Wiley","article_type":"review","page":"1379-1392","quality_controlled":"1","publication_status":"published","date_created":"2022-08-25T08:49:25Z","article_processing_charge":"No","title":"Photochemical strategies for carbon–heteroatom bond formation","intvolume":"      2020","_id":"11969","scopus_import":"1","author":[{"full_name":"Cavedon, Cristian","first_name":"Cristian","last_name":"Cavedon"},{"full_name":"Seeberger, Peter H.","first_name":"Peter H.","last_name":"Seeberger"},{"id":"93e5e5b2-0da6-11ed-8a41-af589a024726","full_name":"Pieber, Bartholomäus","orcid":"0000-0001-8689-388X","last_name":"Pieber","first_name":"Bartholomäus"}],"issue":"10","volume":2020,"extern":"1","doi":"10.1002/ejoc.201901173","day":"15","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."}],"date_updated":"2023-02-21T10:09:47Z","citation":{"short":"C. Cavedon, P.H. Seeberger, B. Pieber, European Journal of Organic Chemistry 2020 (2020) 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>.","ista":"Cavedon C, Seeberger PH, Pieber B. 2020. Photochemical strategies for carbon–heteroatom bond formation. European Journal of Organic Chemistry. 2020(10), 1379–1392.","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>","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.","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>."},"year":"2020"},{"keyword":["Organic Chemistry","Physical and Theoretical Chemistry"],"language":[{"iso":"eng"}],"publication":"European Journal of Organic Chemistry","oa_version":"Published Version","month":"08","main_file_link":[{"url":"https://doi.org/10.1002/ejoc.202000692","open_access":"1"}],"status":"public","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","type":"journal_article","date_published":"2020-08-09T00:00:00Z","publication_identifier":{"issn":["1434-193X","1099-0690"]},"oa":1,"quality_controlled":"1","page":"4499-4509","publisher":"Wiley","article_type":"original","scopus_import":"1","_id":"12939","issue":"29","author":[{"full_name":"Karg, Cornelia A.","last_name":"Karg","first_name":"Cornelia A."},{"full_name":"Wang, Pengyu","first_name":"Pengyu","last_name":"Wang"},{"last_name":"Kluibenschedl","first_name":"Florian","full_name":"Kluibenschedl, Florian","id":"7499e70e-eb2c-11ec-b98b-f925648bc9d9"},{"full_name":"Müller, Thomas","last_name":"Müller","first_name":"Thomas"},{"first_name":"Lars","last_name":"Allmendinger","full_name":"Allmendinger, Lars"},{"first_name":"Angelika M.","last_name":"Vollmar","full_name":"Vollmar, Angelika M."},{"full_name":"Moser, Simone","first_name":"Simone","last_name":"Moser"}],"date_created":"2023-05-10T14:49:30Z","article_processing_charge":"No","publication_status":"published","intvolume":"      2020","title":"Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells","volume":2020,"extern":"1","year":"2020","citation":{"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.","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.","mla":"Karg, Cornelia A., et al. “Phylloxanthobilins Are Abundant Linear Tetrapyrroles from Chlorophyll Breakdown with Activities against Cancer Cells.” <i>European Journal of Organic Chemistry</i>, vol. 2020, no. 29, Wiley, 2020, pp. 4499–509, doi:<a href=\"https://doi.org/10.1002/ejoc.202000692\">10.1002/ejoc.202000692</a>.","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.” <i>European Journal of Organic Chemistry</i>. Wiley, 2020. <a href=\"https://doi.org/10.1002/ejoc.202000692\">https://doi.org/10.1002/ejoc.202000692</a>.","ieee":"C. A. Karg <i>et al.</i>, “Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells,” <i>European Journal of Organic Chemistry</i>, vol. 2020, no. 29. Wiley, pp. 4499–4509, 2020.","apa":"Karg, C. A., Wang, P., Kluibenschedl, F., Müller, T., Allmendinger, L., Vollmar, A. M., &#38; Moser, S. (2020). Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. <i>European Journal of Organic Chemistry</i>. Wiley. <a href=\"https://doi.org/10.1002/ejoc.202000692\">https://doi.org/10.1002/ejoc.202000692</a>","ama":"Karg CA, Wang P, Kluibenschedl F, et al. Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. <i>European Journal of Organic Chemistry</i>. 2020;2020(29):4499-4509. doi:<a href=\"https://doi.org/10.1002/ejoc.202000692\">10.1002/ejoc.202000692</a>"},"date_updated":"2023-05-15T07:57:14Z","day":"09","doi":"10.1002/ejoc.202000692","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."}]}]