[{"author":[{"full_name":"Madani, Amiera","last_name":"Madani","first_name":"Amiera"},{"full_name":"Anghileri, Lucia","last_name":"Anghileri","first_name":"Lucia"},{"full_name":"Heydenreich, Matthias","first_name":"Matthias","last_name":"Heydenreich"},{"full_name":"Möller, Heiko M.","first_name":"Heiko M.","last_name":"Möller"},{"id":"93e5e5b2-0da6-11ed-8a41-af589a024726","orcid":"0000-0001-8689-388X","full_name":"Pieber, Bartholomäus","last_name":"Pieber","first_name":"Bartholomäus"}],"day":"17","title":"Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","publisher":"American Chemical Society","publication":"Organic Letters","article_type":"original","scopus_import":"1","article_processing_charge":"No","publication_identifier":{"eissn":["1523-7052"],"issn":["1523-7060"]},"doi":"10.1021/acs.orglett.2c02050","quality_controlled":"1","issue":"29","language":[{"iso":"eng"}],"page":"5376–5380","oa_version":"Published Version","month":"07","type":"journal_article","abstract":[{"text":"We present a divergent strategy for the fluorination of phenylacetic acid derivatives that is induced by a charge-transfer complex between Selectfluor and 4-(dimethylamino)pyridine. A comprehensive investigation of the conditions revealed a critical role of the solvent on the reaction outcome. In the presence of water, decarboxylative fluorination through a single-electron oxidation is dominant. Non-aqueous conditions result in the clean formation of α-fluoro-α-arylcarboxylic acids.","lang":"eng"}],"date_updated":"2023-05-08T08:39:34Z","volume":24,"date_created":"2022-09-08T11:34:30Z","year":"2022","_id":"12067","oa":1,"publication_status":"published","date_published":"2022-07-17T00:00:00Z","main_file_link":[{"open_access":"1","url":"https://doi.org/10.26434/chemrxiv-2022-mstv5"}],"status":"public","intvolume":"        24","extern":"1","citation":{"ama":"Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. <i>Organic Letters</i>. 2022;24(29):5376–5380. doi:<a href=\"https://doi.org/10.1021/acs.orglett.2c02050\">10.1021/acs.orglett.2c02050</a>","mla":"Madani, Amiera, et al. “Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch.” <i>Organic Letters</i>, vol. 24, no. 29, American Chemical Society, 2022, pp. 5376–5380, doi:<a href=\"https://doi.org/10.1021/acs.orglett.2c02050\">10.1021/acs.orglett.2c02050</a>.","ista":"Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. 2022. Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. Organic Letters. 24(29), 5376–5380.","apa":"Madani, A., Anghileri, L., Heydenreich, M., Möller, H. M., &#38; Pieber, B. (2022). Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. <i>Organic Letters</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.orglett.2c02050\">https://doi.org/10.1021/acs.orglett.2c02050</a>","ieee":"A. Madani, L. Anghileri, M. Heydenreich, H. M. Möller, and B. Pieber, “Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch,” <i>Organic Letters</i>, vol. 24, no. 29. American Chemical Society, pp. 5376–5380, 2022.","chicago":"Madani, Amiera, Lucia Anghileri, Matthias Heydenreich, Heiko M. Möller, and Bartholomäus Pieber. “Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch.” <i>Organic Letters</i>. American Chemical Society, 2022. <a href=\"https://doi.org/10.1021/acs.orglett.2c02050\">https://doi.org/10.1021/acs.orglett.2c02050</a>.","short":"A. Madani, L. Anghileri, M. Heydenreich, H.M. Möller, B. Pieber, Organic Letters 24 (2022) 5376–5380."}},{"year":"2021","_id":"11981","type":"journal_article","oa_version":"Published Version","month":"01","date_updated":"2023-02-21T10:10:16Z","abstract":[{"lang":"eng","text":"The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow."}],"page":"514-518","date_created":"2022-08-25T11:13:05Z","volume":23,"external_id":{"pmid":["33400534"]},"status":"public","citation":{"short":"C. Cavedon, E.T. Sletten, A. Madani, O. Niemeyer, P.H. Seeberger, B. Pieber, Organic Letters 23 (2021) 514–518.","ieee":"C. Cavedon, E. T. Sletten, A. Madani, O. Niemeyer, P. H. Seeberger, and B. Pieber, “Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups,” <i>Organic Letters</i>, vol. 23, no. 2. American Chemical Society, pp. 514–518, 2021.","chicago":"Cavedon, Cristian, Eric T. Sletten, Amiera Madani, Olaf Niemeyer, Peter H. Seeberger, and Bartholomäus Pieber. “Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups.” <i>Organic Letters</i>. American Chemical Society, 2021. <a href=\"https://doi.org/10.1021/acs.orglett.0c04026\">https://doi.org/10.1021/acs.orglett.0c04026</a>.","ista":"Cavedon C, Sletten ET, Madani A, Niemeyer O, Seeberger PH, Pieber B. 2021. Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups. Organic Letters. 23(2), 514–518.","mla":"Cavedon, Cristian, et al. “Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups.” <i>Organic Letters</i>, vol. 23, no. 2, American Chemical Society, 2021, pp. 514–18, doi:<a href=\"https://doi.org/10.1021/acs.orglett.0c04026\">10.1021/acs.orglett.0c04026</a>.","apa":"Cavedon, C., Sletten, E. T., Madani, A., Niemeyer, O., Seeberger, P. H., &#38; Pieber, B. (2021). Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups. <i>Organic Letters</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.orglett.0c04026\">https://doi.org/10.1021/acs.orglett.0c04026</a>","ama":"Cavedon C, Sletten ET, Madani A, Niemeyer O, Seeberger PH, Pieber B. Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups. <i>Organic Letters</i>. 2021;23(2):514-518. doi:<a href=\"https://doi.org/10.1021/acs.orglett.0c04026\">10.1021/acs.orglett.0c04026</a>"},"extern":"1","intvolume":"        23","oa":1,"publication_status":"published","main_file_link":[{"open_access":"1","url":"https://doi.org/10.1021/acs.orglett.0c04026"}],"date_published":"2021-01-15T00:00:00Z","pmid":1,"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","publisher":"American Chemical Society","article_type":"letter_note","scopus_import":"1","article_processing_charge":"No","publication":"Organic Letters","day":"15","author":[{"last_name":"Cavedon","first_name":"Cristian","full_name":"Cavedon, Cristian"},{"last_name":"Sletten","first_name":"Eric T.","full_name":"Sletten, Eric T."},{"first_name":"Amiera","last_name":"Madani","full_name":"Madani, Amiera"},{"first_name":"Olaf","last_name":"Niemeyer","full_name":"Niemeyer, Olaf"},{"full_name":"Seeberger, Peter H.","first_name":"Peter H.","last_name":"Seeberger"},{"full_name":"Pieber, Bartholomäus","orcid":"0000-0001-8689-388X","id":"93e5e5b2-0da6-11ed-8a41-af589a024726","last_name":"Pieber","first_name":"Bartholomäus"}],"title":"Visible-light-mediated oxidative debenzylation enables the use of benzyl ethers as temporary protecting groups","issue":"2","language":[{"iso":"eng"}],"publication_identifier":{"issn":["1523-7060"],"eissn":["1523-7052"]},"quality_controlled":"1","doi":"10.1021/acs.orglett.0c04026"},{"publication_status":"published","oa":1,"date_published":"2019-07-05T00:00:00Z","main_file_link":[{"open_access":"1","url":"https://doi.org/10.1021/acs.orglett.9b01957"}],"external_id":{"pmid":["31247752"]},"status":"public","extern":"1","intvolume":"        21","citation":{"chicago":"Cavedon, Cristian, Amiera Madani, Peter H. Seeberger, and Bartholomäus Pieber. “Semiheterogeneous Dual Nickel/Photocatalytic (Thio)Etherification Using Carbon Nitrides.” <i>Organic Letters</i>. American Chemical Society, 2019. <a href=\"https://doi.org/10.1021/acs.orglett.9b01957\">https://doi.org/10.1021/acs.orglett.9b01957</a>.","ieee":"C. Cavedon, A. Madani, P. H. Seeberger, and B. Pieber, “Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon nitrides,” <i>Organic Letters</i>, vol. 21, no. 13. American Chemical Society, pp. 5331–5334, 2019.","short":"C. Cavedon, A. Madani, P.H. Seeberger, B. Pieber, Organic Letters 21 (2019) 5331–5334.","ama":"Cavedon C, Madani A, Seeberger PH, Pieber B. Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon nitrides. <i>Organic Letters</i>. 2019;21(13):5331-5334. doi:<a href=\"https://doi.org/10.1021/acs.orglett.9b01957\">10.1021/acs.orglett.9b01957</a>","apa":"Cavedon, C., Madani, A., Seeberger, P. H., &#38; Pieber, B. (2019). Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon nitrides. <i>Organic Letters</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.orglett.9b01957\">https://doi.org/10.1021/acs.orglett.9b01957</a>","mla":"Cavedon, Cristian, et al. “Semiheterogeneous Dual Nickel/Photocatalytic (Thio)Etherification Using Carbon Nitrides.” <i>Organic Letters</i>, vol. 21, no. 13, American Chemical Society, 2019, pp. 5331–34, doi:<a href=\"https://doi.org/10.1021/acs.orglett.9b01957\">10.1021/acs.orglett.9b01957</a>.","ista":"Cavedon C, Madani A, Seeberger PH, Pieber B. 2019. Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon nitrides. Organic Letters. 21(13), 5331–5334."},"page":"5331-5334","month":"07","type":"journal_article","oa_version":"Published Version","date_updated":"2023-02-21T10:10:19Z","abstract":[{"lang":"eng","text":"A carbon nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable for the coupling of aryl iodides with thiols as well."}],"volume":21,"date_created":"2022-08-25T11:18:00Z","year":"2019","_id":"11982","publication_identifier":{"issn":["1523-7060"],"eissn":["1523-7052"]},"doi":"10.1021/acs.orglett.9b01957","quality_controlled":"1","issue":"13","language":[{"iso":"eng"}],"author":[{"last_name":"Cavedon","first_name":"Cristian","full_name":"Cavedon, Cristian"},{"full_name":"Madani, Amiera","first_name":"Amiera","last_name":"Madani"},{"full_name":"Seeberger, Peter H.","first_name":"Peter H.","last_name":"Seeberger"},{"id":"93e5e5b2-0da6-11ed-8a41-af589a024726","orcid":"0000-0001-8689-388X","full_name":"Pieber, Bartholomäus","last_name":"Pieber","first_name":"Bartholomäus"}],"day":"05","title":"Semiheterogeneous dual nickel/photocatalytic (thio)etherification using carbon nitrides","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","publisher":"American Chemical Society","pmid":1,"publication":"Organic Letters","article_type":"letter_note","article_processing_charge":"No","scopus_import":"1"},{"status":"public","external_id":{"pmid":["26902154"]},"extern":"1","intvolume":"        18","citation":{"ieee":"B. Pieber and C. O. Kappe, “Generation and synthetic application of trifluoromethyl diazomethane utilizing continuous flow technologies,” <i>Organic Letters</i>, vol. 18, no. 5. American Chemical Society, pp. 1076–1079, 2016.","chicago":"Pieber, Bartholomäus, and C. Oliver Kappe. “Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies.” <i>Organic Letters</i>. American Chemical Society, 2016. <a href=\"https://doi.org/10.1021/acs.orglett.6b00194\">https://doi.org/10.1021/acs.orglett.6b00194</a>.","short":"B. Pieber, C.O. Kappe, Organic Letters 18 (2016) 1076–1079.","ama":"Pieber B, Kappe CO. Generation and synthetic application of trifluoromethyl diazomethane utilizing continuous flow technologies. <i>Organic Letters</i>. 2016;18(5):1076-1079. doi:<a href=\"https://doi.org/10.1021/acs.orglett.6b00194\">10.1021/acs.orglett.6b00194</a>","mla":"Pieber, Bartholomäus, and C. Oliver Kappe. “Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies.” <i>Organic Letters</i>, vol. 18, no. 5, American Chemical Society, 2016, pp. 1076–79, doi:<a href=\"https://doi.org/10.1021/acs.orglett.6b00194\">10.1021/acs.orglett.6b00194</a>.","ista":"Pieber B, Kappe CO. 2016. Generation and synthetic application of trifluoromethyl diazomethane utilizing continuous flow technologies. Organic Letters. 18(5), 1076–1079.","apa":"Pieber, B., &#38; Kappe, C. O. (2016). Generation and synthetic application of trifluoromethyl diazomethane utilizing continuous flow technologies. <i>Organic Letters</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.orglett.6b00194\">https://doi.org/10.1021/acs.orglett.6b00194</a>"},"publication_status":"published","date_published":"2016-03-04T00:00:00Z","year":"2016","_id":"11983","page":"1076-1079","abstract":[{"lang":"eng","text":"A continuous process for the synthesis and inline separation of anhydrous trifluoromethyl diazomethane in a single continuous flow process is presented. The diazo building block is generated from the corresponding amine and NaNO2 under acidic, aqueous conditions and subsequently diffuses through a gas-permeable membrane into an organic stream. To avoid storage and transportation of the hazardous compound, a representative downstream process in a packed-bed reactor yielding highly functionalized building blocks was developed."}],"date_updated":"2023-02-21T10:10:21Z","month":"03","type":"journal_article","oa_version":"None","volume":18,"date_created":"2022-08-25T11:22:20Z","language":[{"iso":"eng"}],"issue":"5","publication_identifier":{"issn":["1523-7060"],"eissn":["1523-7052"]},"doi":"10.1021/acs.orglett.6b00194","quality_controlled":"1","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","publisher":"American Chemical Society","pmid":1,"publication":"Organic Letters","article_processing_charge":"No","scopus_import":"1","article_type":"letter_note","author":[{"first_name":"Bartholomäus","last_name":"Pieber","id":"93e5e5b2-0da6-11ed-8a41-af589a024726","orcid":"0000-0001-8689-388X","full_name":"Pieber, Bartholomäus"},{"full_name":"Kappe, C. Oliver","first_name":"C. Oliver","last_name":"Kappe"}],"day":"04","title":"Generation and synthetic application of trifluoromethyl diazomethane utilizing continuous flow technologies"}]