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Herein, we report a H-bonded EDA (H-EDA) donor catalysis system, employing thiols as donor catalysts to achieve Markovnikov hydroarylation and hydroxyalkylation of N-acyl enamines under redox-neutral conditions. This protocol proceeds under metal-free, base-free, and redox auxiliary-free conditions with complete atom economy. Mechanistic studies reveal that the reaction proceeds through oxidative nucleophilic coupling enabled by a photoinduced H-EDA complex via SET and 1,5-H-shift. The protocol features broad substrate scope, excellent regioselectivity, and gram-scale scalability. This work establishes a general H-EDA donor catalytic platform and redefines EDA donor catalysis beyond conventional redox auxiliary (RA)-mediated activation.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03283","type":"journal-article","created":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T04:01:51Z","timestamp":1787198511000},"page":"11099-11104","source":"Crossref","is-referenced-by-count":0,"title":["Hydrogen-Bonded\nElectron Donor\u2013Acceptor Complex\nEnables Markovnikov Hydroarylation and Hydroxyalkylation of\n                    <i>N<\/i>\n                    -Acyl Enamines"],"prefix":"10.1021","volume":"28","author":[{"given":"Zhenda","family":"Su","sequence":"first","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tingtao","family":"Yan","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1551-267X","authenticated-orcid":true,"given":"Kelu","family":"Yan","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinkai","family":"Shi","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8741-645X","authenticated-orcid":true,"given":"Bingwen","family":"Li","sequence":"additional","affiliation":[{"name":"Dezhou University , , , ,","place":["Dezhou, Shandong, China, 253023"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mingming","family":"Yu","sequence":"additional","affiliation":[{"name":"Zhejiang Sci-Tech University, Xiasha West Higher Education District , , ,","place":["Hangzhou, China, 310018"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dandan","family":"Li","sequence":"additional","affiliation":[{"name":"Xuchang University , , , ,","place":["Xuchang, Henan, China, 461000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianjing","family":"Yang","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4431-9158","authenticated-orcid":true,"given":"Jiangwei","family":"Wen","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,19]]},"reference":[{"key":"2026090409102112300_cit1a","doi-asserted-by":"publisher","first-page":"1389","DOI":"10.1021\/acscatal.5b02386","article-title":"Organic Synthesis Enabled by Light-Irradiation of EDA\nComplexes: Theoretical Background and Synthetic Applications","volume":"6","author":"Lima","year":"2016","journal-title":"ACS Catal."},{"key":"2026090409102112300_cit1b","doi-asserted-by":"publisher","first-page":"5461","DOI":"10.1021\/jacs.0c01416","article-title":"Synthetic Methods Driven by the Photoactivity\nof Electron Donor\u2013Acceptor Complexes","volume":"142","author":"Crisenza","year":"2020","journal-title":"J. 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