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It is often solved by adding another component\u2010a sacrificial agent\u2010whose role is to convert the catalyst back into its original oxidation state. However, an additive may cause a side reaction thus decreasing the selectivity and overall efficiency. Herein, we present a novel approach towards chemoselective photooxidation reactions based on suitable solvent\u2010acetonitrile acting simultaneously as an electron acceptor for catalyst recovery, and on anaerobic conditions. This is allowed by the unique properties of the catalyst, 7,8\u2010dimethoxy\u20103\u2010methyl\u20105\u2010phenyl\u20105\u2010deazaflavinium chloride existing in both strongly oxidizing and reducing forms, whose strength is increased by excitation with visible light. Usefulness of this system is demonstrated in chemoselective dehydrogenations of 4\u2010methoxy\u2010 and 4\u2010chlorobenzyl alcohols to aldehydes without over\u2010oxidation to benzoic acids achieving yields up to 70\u2009%. 4\u2010Substituted 1\u2010phenylethanols were oxidized to ketones with yields 80\u2013100\u2009% and, moreover, with yields 31\u201098\u2009% in the presence of benzylic methyl group, diphenylmethane or thioanisole which are readily oxidized in the presence of oxygen but these were untouched with our system. Mechanistic studies based on UV\u2010Vis spectro\u2010electrochemistry, EPR and time\u2010resolved spectroscopy measurements showed that the process involving an electron release from an excited deazaflavin radical to acetonitrile under formation of solvated electron is crucial for the catalyst recovery.<\/jats:p>","DOI":"10.1002\/chem.202202487","type":"journal-article","created":{"date-parts":[[2022,8,30]],"date-time":"2022-08-30T13:11:02Z","timestamp":1661865062000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Highly Chemoselective Catalytic Photooxidations by Using Solvent as a Sacrificial Electron Acceptor"],"prefix":"10.1002","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8014-1484","authenticated-orcid":false,"given":"R\u00f3bert","family":"Obert\u00edk","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry University of Chemistry and Technology, Prague  Technick\u00e1 5 166 28 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4127-0376","authenticated-orcid":false,"given":"Josef","family":"Chudoba","sequence":"additional","affiliation":[{"name":"Central Laboratories University of Chemistry and Technology, Prague  Technick\u00e1 5 166 28 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8113-0709","authenticated-orcid":false,"given":"Ji\u0159\u00ed","family":"\u0160turala","sequence":"additional","affiliation":[{"name":"Department of Inorganic Chemistry University of Chemistry and Technology, Prague  Technick\u00e1 5 166 28 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0116-3824","authenticated-orcid":false,"given":"J\u00e1n","family":"Tar\u00e1bek","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Academy of Science of the Czech Republic  Flemingovo n\u00e1m. 2 16610 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3697-5593","authenticated-orcid":false,"given":"Lucie","family":"Ludv\u00edkov\u00e1","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Academy of Science of the Czech Republic  Flemingovo n\u00e1m. 2 16610 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8092-7268","authenticated-orcid":false,"given":"Tom\u00e1\u0161","family":"Slanina","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Academy of Science of the Czech Republic  Flemingovo n\u00e1m. 2 16610 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6131-4850","authenticated-orcid":false,"given":"Burkhard","family":"K\u00f6nig","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry University of Regensburg Universit\u00e4tsstrasse 31  93040 Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8584-7715","authenticated-orcid":false,"given":"Radek","family":"Cibulka","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University of Chemistry and Technology, Prague  Technick\u00e1 5 166 28 Prague 6 Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,10,5]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00125B"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800182r"},{"key":"e_1_2_8_4_1","unstructured":"\u00a0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00547"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b823399c"},{"key":"e_1_2_8_7_1","unstructured":"\u00a0"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202200704"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2gc00027j"},{"key":"e_1_2_8_10_1","unstructured":"\u00a0"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201901687"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201800013"},{"key":"e_1_2_8_13_1","unstructured":"\u00a0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.c21-00092"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201804946"},{"key":"e_1_2_8_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201804946"},{"key":"e_1_2_8_16_2","doi-asserted-by":"crossref","unstructured":"M.\u2005N. 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